# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm #TrackingRef 'Complex_1a.cif' _journal_coden_Cambridge 1350 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. Alexandre N. Sobolev' _publ_contact_author_address ; Chemistry Section, M313, School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; _publ_contact_author_email Alexandre.Sobolev@uwa.edu.au _publ_contact_author_fax '+618 6488 1005' _publ_contact_author_phone '+618 6488 3157' _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this submission for publication as a New paper in Chemical Communication. The figures, chemical structure diagram (scheme), Transfer of Copyright Agreement form and structure factor listing will be sent on receipt of your acknowledgement email or letter. ; # 2. PROCESSING SUMMARY (IUCr Office Use Only) # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? #<< paper title text ; _publ_section_title_footnote ; ? #<< paper footnote text ; loop_ _publ_author_name _publ_author_address 'Irene Ling' ; Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia ; 'Yatimah Alias' ; Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia ; 'Alexandre N. Sobolev' ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; 'Colin L. Raston' ; Chemistry Section, M313, School of Biomedical and Chemical Sciences, University of Western Australia, 35 Stirling Highway, Crawley, 6009, W.A., Australia ; # 4. TEXT _publ_section_synopsis ; ? #<< synopsis if FI,CI,CM,CO papers ; _publ_section_abstract ; ? #<< abstract text ; _publ_section_comment ; ? #<< scientific commentary text ; _publ_section_exptl_prep ; ? #<< material & crystal preparation text ; _publ_section_acknowledgements ; ? #<< acknowledgements text ; _publ_section_references ; Barbour, L. J. (2001). J. Supramol. Chem., 1, 189-191. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; # 5. CHEMICAL DATA _publ_section_figure_captions ; ? #<< figure captions ; #============================================================================== data_110808g _database_code_depnum_ccdc_archive 'CCDC 760636' #TrackingRef 'Complex_1a.cif' # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 P, F6 P' _chemical_formula_sum 'C19 H18 F6 P2' _chemical_formula_weight 422.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 21.0221(13) _cell_length_b 13.0920(6) _cell_length_c 14.5647(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.382(7) _cell_angle_gamma 90.00 _cell_volume 3781.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8698 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 67.2 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method ? _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 2.638 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6938 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41383 _diffrn_reflns_av_R_equivalents 0.0737 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 67.22 _reflns_number_total 6729 _reflns_number_gt 5162 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1200P)^2^+50.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6729 _refine_ls_number_parameters 527 _refine_ls_number_restraints 80 _refine_ls_R_factor_all 0.1241 _refine_ls_R_factor_gt 0.1045 _refine_ls_wR_factor_ref 0.3091 _refine_ls_wR_factor_gt 0.2974 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1A P 0.38531(9) 0.19852(13) 0.48741(13) 0.0254(4) Uani 1 1 d . . . C1A C 0.4627(4) 0.1513(6) 0.5692(6) 0.0336(17) Uani 1 1 d . . . H1AA H 0.4580 0.0785 0.5812 0.050 Uiso 1 1 calc R . . H1AB H 0.4742 0.1887 0.6309 0.050 Uiso 1 1 calc R . . H1AC H 0.4985 0.1606 0.5408 0.050 Uiso 1 1 calc R . . C11A C 0.3945(4) 0.3314(6) 0.4662(5) 0.0294(15) Uani 1 1 d . . . C12A C 0.4138(4) 0.3974(6) 0.5464(6) 0.0350(17) Uani 1 1 d . . . H12A H 0.4215 0.3715 0.6101 0.042 Uiso 1 1 calc R . . C13A C 0.4216(4) 0.5006(6) 0.5324(7) 0.0397(19) Uani 1 1 d . . . H13A H 0.4339 0.5457 0.5866 0.048 Uiso 1 1 calc R . . C14A C 0.4118(4) 0.5382(6) 0.4407(6) 0.0396(19) Uani 1 1 d . . . H14A H 0.4179 0.6091 0.4321 0.048 Uiso 1 1 calc R . . C15A C 0.3932(5) 0.4746(7) 0.3613(7) 0.047(2) Uani 1 1 d . . . H15A H 0.3864 0.5015 0.2981 0.057 Uiso 1 1 calc R . . C16A C 0.3843(4) 0.3699(6) 0.3733(6) 0.0381(18) Uani 1 1 d . . . H16A H 0.3715 0.3256 0.3186 0.046 Uiso 1 1 calc R . . C21A C 0.3620(4) 0.1275(5) 0.3762(5) 0.0267(15) Uani 1 1 d . . . C22A C 0.4103(4) 0.0694(6) 0.3523(6) 0.0345(17) Uani 1 1 d . . . H22A H 0.4559 0.0689 0.3942 0.041 Uiso 1 1 calc R . . C23A C 0.3914(4) 0.0135(7) 0.2681(6) 0.0400(19) Uani 1 1 d . . . H23A H 0.4242 -0.0257 0.2518 0.048 Uiso 1 1 calc R . . C24A C 0.3252(5) 0.0132(7) 0.2066(6) 0.045(2) Uani 1 1 d . . . H24A H 0.3126 -0.0263 0.1486 0.054 Uiso 1 1 calc R . . C25A C 0.2779(4) 0.0700(7) 0.2295(6) 0.0404(19) Uani 1 1 d . . . H25A H 0.2326 0.0703 0.1866 0.049 Uiso 1 1 calc R . . C26A C 0.2954(4) 0.1273(7) 0.3146(6) 0.0393(18) Uani 1 1 d . . . H26A H 0.2622 0.1658 0.3305 0.047 Uiso 1 1 calc R . . C31A C 0.3204(4) 0.1846(6) 0.5405(5) 0.0300(15) Uani 1 1 d . . . C32A C 0.3179(4) 0.0965(6) 0.5933(6) 0.0351(17) Uani 1 1 d . . . H32A H 0.3515 0.0453 0.6026 0.042 Uiso 1 1 calc R . . C33A C 0.2672(4) 0.0841(7) 0.6315(6) 0.0394(19) Uani 1 1 d . . . H33A H 0.2663 0.0244 0.6681 0.047 Uiso 1 1 calc R . . C34A C 0.2175(4) 0.1560(6) 0.6182(6) 0.0408(19) Uani 1 1 d . . . H34A H 0.1830 0.1466 0.6459 0.049 Uiso 1 1 calc R . . C35A C 0.2184(4) 0.2430(7) 0.5633(8) 0.050(2) Uani 1 1 d . . . H35A H 0.1837 0.2927 0.5523 0.060 Uiso 1 1 calc R . . C36A C 0.2697(4) 0.2566(6) 0.5251(7) 0.046(2) Uani 1 1 d . . . H36A H 0.2703 0.3160 0.4879 0.055 Uiso 1 1 calc R . . P1B P 0.12215(9) 0.82365(13) 0.10465(13) 0.0253(4) Uani 1 1 d . . . C1B C 0.0422(4) 0.8753(6) 0.0994(6) 0.0330(16) Uani 1 1 d . . . H1BA H 0.0260 0.8401 0.1466 0.049 Uiso 1 1 calc R . . H1BB H 0.0098 0.8659 0.0338 0.049 Uiso 1 1 calc R . . H1BC H 0.0472 0.9484 0.1149 0.049 Uiso 1 1 calc R . . C11B C 0.1106(3) 0.6898(6) 0.0770(5) 0.0286(15) Uani 1 1 d . . . C12B C 0.1105(4) 0.6224(6) 0.1515(6) 0.0346(17) Uani 1 1 d . . . H12B H 0.1216 0.6457 0.2167 0.042 Uiso 1 1 calc R . . C13B C 0.0939(4) 0.5212(6) 0.1285(7) 0.043(2) Uani 1 1 d . . . H13B H 0.0927 0.4750 0.1781 0.052 Uiso 1 1 calc R . . C14B C 0.0791(4) 0.4863(6) 0.0337(6) 0.0365(18) Uani 1 1 d . . . H14B H 0.0691 0.4162 0.0192 0.044 Uiso 1 1 calc R . . C15B C 0.0789(4) 0.5532(6) -0.0394(6) 0.0374(18) Uani 1 1 d . . . H15B H 0.0676 0.5295 -0.1045 0.045 Uiso 1 1 calc R . . C16B C 0.0953(4) 0.6563(5) -0.0178(6) 0.0322(16) Uani 1 1 d . . . H16B H 0.0958 0.7026 -0.0678 0.039 Uiso 1 1 calc R . . C21B C 0.1530(3) 0.8873(5) 0.0187(5) 0.0255(14) Uani 1 1 d . . . C22B C 0.1248(4) 0.9803(6) -0.0232(6) 0.0386(18) Uani 1 1 d . . . H22B H 0.0878 1.0086 -0.0083 0.046 Uiso 1 1 calc R . . C23B C 0.1508(5) 1.0308(7) -0.0862(7) 0.048(2) Uani 1 1 d . . . H23B H 0.1305 1.0927 -0.1158 0.058 Uiso 1 1 calc R . . C24B C 0.2053(5) 0.9932(7) -0.1066(6) 0.046(2) Uani 1 1 d . . . H24B H 0.2229 1.0289 -0.1497 0.056 Uiso 1 1 calc R . . C25B C 0.2351(4) 0.9017(7) -0.0635(6) 0.0414(19) Uani 1 1 d . . . H25B H 0.2732 0.8753 -0.0767 0.050 Uiso 1 1 calc R . . C26B C 0.2088(4) 0.8501(6) -0.0018(6) 0.0323(16) Uani 1 1 d . . . H26B H 0.2291 0.7880 0.0273 0.039 Uiso 1 1 calc R . . C31B C 0.1822(3) 0.8399(6) 0.2242(5) 0.0291(15) Uani 1 1 d . . . C32B C 0.1675(4) 0.9064(7) 0.2913(5) 0.0360(17) Uani 1 1 d . . . H32B H 0.1246 0.9382 0.2753 0.043 Uiso 1 1 calc R . . C33B C 0.2166(4) 0.9245(7) 0.3806(6) 0.0411(19) Uani 1 1 d . . . H33B H 0.2074 0.9690 0.4262 0.049 Uiso 1 1 calc R . . C34B C 0.2785(4) 0.8782(7) 0.4033(6) 0.043(2) Uani 1 1 d . . . H34B H 0.3119 0.8908 0.4647 0.051 Uiso 1 1 calc R . . C35B C 0.2930(4) 0.8133(7) 0.3378(6) 0.044(2) Uani 1 1 d . . . H35B H 0.3361 0.7820 0.3546 0.053 Uiso 1 1 calc R . . C36B C 0.2453(4) 0.7937(6) 0.2482(6) 0.0375(18) Uani 1 1 d . . . H36B H 0.2554 0.7491 0.2035 0.045 Uiso 1 1 calc R . . P2A P 0.42152(9) 0.80347(15) 0.66622(15) 0.0334(5) Uani 1 1 d D . . F1A F 0.3862(5) 0.7016(6) 0.6332(11) 0.102(5) Uani 0.762(13) 1 d P A 1 F2A F 0.4573(4) 0.9098(7) 0.7098(8) 0.073(3) Uani 0.762(13) 1 d P A 1 F3A F 0.4249(3) 0.8353(10) 0.5664(5) 0.073(3) Uani 0.762(13) 1 d P A 1 F4A F 0.3500(3) 0.8573(5) 0.6450(5) 0.0359(16) Uani 0.762(13) 1 d P A 1 F5A F 0.4180(4) 0.7840(8) 0.7756(6) 0.073(3) Uani 0.762(13) 1 d P A 1 F6A F 0.4943(4) 0.7544(6) 0.6985(7) 0.064(3) Uani 0.762(13) 1 d P A 1 F1A' F 0.3732(6) 0.7397(11) 0.5727(8) 0.039(3) Uiso 0.238(13) 1 d PD A 2 F2A' F 0.4704(6) 0.8659(11) 0.7506(9) 0.039(3) Uiso 0.238(13) 1 d PD A 2 F3A' F 0.4253(7) 0.8917(10) 0.5889(10) 0.039(3) Uiso 0.238(13) 1 d PD A 2 F4A' F 0.3573(6) 0.8567(11) 0.6771(12) 0.039(3) Uiso 0.238(13) 1 d PD A 2 F5A' F 0.4174(7) 0.7132(10) 0.7344(10) 0.039(3) Uiso 0.238(13) 1 d PD A 2 F6A' F 0.4853(5) 0.7488(10) 0.6458(11) 0.039(3) Uiso 0.238(13) 1 d PD A 2 P2B P 0.06835(11) 0.19747(15) 0.21567(16) 0.0386(5) Uani 1 1 d D . . F1B F 0.1370(3) 0.2587(5) 0.2670(4) 0.0494(18) Uani 0.822(10) 1 d P B 1 F2B F 0.0016(3) 0.1388(5) 0.1567(5) 0.062(2) Uani 0.822(10) 1 d P B 1 F3B F 0.0788(4) 0.1341(7) 0.3084(6) 0.082(3) Uani 0.822(10) 1 d P B 1 F4B F 0.0277(4) 0.2844(6) 0.2439(6) 0.069(2) Uani 0.822(10) 1 d P B 1 F5B F 0.0614(3) 0.2617(6) 0.1161(4) 0.0553(19) Uani 0.822(10) 1 d P B 1 F6B F 0.1121(4) 0.1154(5) 0.1767(6) 0.064(2) Uani 0.822(10) 1 d P B 1 F1B' F 0.0963(15) 0.3104(11) 0.221(2) 0.116(10) Uiso 0.178(10) 1 d PD B 2 F2B' F 0.0387(16) 0.0835(12) 0.214(2) 0.116(10) Uiso 0.178(10) 1 d PD B 2 F3B' F 0.0722(16) 0.206(3) 0.3284(9) 0.116(10) Uiso 0.178(10) 1 d PD B 2 F4B' F -0.0075(7) 0.241(2) 0.184(2) 0.116(10) Uiso 0.178(10) 1 d PD B 2 F5B' F 0.0627(15) 0.188(3) 0.1055(9) 0.116(10) Uiso 0.178(10) 1 d PD B 2 F6B' F 0.1426(8) 0.153(2) 0.250(2) 0.116(10) Uiso 0.178(10) 1 d PD B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1A 0.0264(9) 0.0195(8) 0.0281(9) -0.0006(7) 0.0062(7) 0.0015(7) C1A 0.031(4) 0.029(4) 0.035(4) -0.001(3) 0.004(3) 0.007(3) C11A 0.027(4) 0.024(4) 0.037(4) 0.002(3) 0.010(3) 0.004(3) C12A 0.044(4) 0.023(4) 0.042(4) -0.002(3) 0.020(4) 0.000(3) C13A 0.045(5) 0.024(4) 0.056(5) -0.005(4) 0.025(4) 0.001(3) C14A 0.034(4) 0.027(4) 0.059(5) 0.005(4) 0.017(4) 0.001(3) C15A 0.050(5) 0.042(5) 0.046(5) 0.011(4) 0.010(4) -0.005(4) C16A 0.041(4) 0.031(4) 0.038(4) 0.000(3) 0.006(3) -0.009(3) C21A 0.029(4) 0.016(3) 0.033(4) -0.002(3) 0.008(3) -0.005(3) C22A 0.030(4) 0.038(4) 0.036(4) -0.003(3) 0.012(3) -0.004(3) C23A 0.043(5) 0.043(5) 0.038(4) -0.007(4) 0.018(4) -0.007(4) C24A 0.057(5) 0.045(5) 0.035(4) -0.010(4) 0.019(4) -0.027(4) C25A 0.036(4) 0.044(5) 0.034(4) 0.003(4) 0.003(3) -0.009(4) C26A 0.031(4) 0.050(5) 0.034(4) 0.002(4) 0.007(3) -0.003(4) C31A 0.033(4) 0.026(4) 0.029(4) -0.003(3) 0.008(3) 0.001(3) C32A 0.040(4) 0.028(4) 0.035(4) 0.004(3) 0.010(3) 0.001(3) C33A 0.040(4) 0.039(5) 0.039(4) 0.003(3) 0.013(4) -0.008(4) C34A 0.040(4) 0.036(4) 0.051(5) -0.015(4) 0.021(4) -0.019(4) C35A 0.037(5) 0.034(5) 0.087(7) -0.006(4) 0.030(5) -0.002(4) C36A 0.046(5) 0.025(4) 0.074(6) 0.012(4) 0.030(5) 0.007(4) P1B 0.0232(9) 0.0222(9) 0.0295(9) 0.0016(7) 0.0075(7) 0.0024(7) C1B 0.032(4) 0.029(4) 0.037(4) 0.002(3) 0.010(3) 0.003(3) C11B 0.019(3) 0.028(4) 0.038(4) 0.005(3) 0.008(3) 0.003(3) C12B 0.038(4) 0.026(4) 0.038(4) 0.003(3) 0.010(3) -0.001(3) C13B 0.040(5) 0.032(4) 0.055(5) 0.014(4) 0.012(4) 0.004(4) C14B 0.020(3) 0.023(4) 0.061(5) -0.001(4) 0.007(3) -0.001(3) C15B 0.034(4) 0.030(4) 0.052(5) -0.012(4) 0.019(4) -0.008(3) C16B 0.032(4) 0.018(3) 0.049(5) 0.000(3) 0.016(3) -0.002(3) C21B 0.030(4) 0.015(3) 0.028(3) -0.002(3) 0.005(3) 0.000(3) C22B 0.041(4) 0.029(4) 0.043(4) 0.012(3) 0.012(4) 0.004(3) C23B 0.056(5) 0.037(5) 0.047(5) 0.013(4) 0.010(4) -0.002(4) C24B 0.060(6) 0.048(5) 0.033(4) 0.000(4) 0.017(4) -0.019(4) C25B 0.048(5) 0.038(5) 0.045(5) -0.011(4) 0.024(4) -0.012(4) C26B 0.028(4) 0.029(4) 0.041(4) -0.002(3) 0.013(3) -0.001(3) C31B 0.025(3) 0.030(4) 0.031(4) 0.004(3) 0.007(3) -0.004(3) C32B 0.032(4) 0.044(5) 0.032(4) -0.001(3) 0.010(3) -0.007(3) C33B 0.043(5) 0.046(5) 0.035(4) -0.003(4) 0.013(4) -0.007(4) C34B 0.042(5) 0.049(5) 0.031(4) 0.009(4) 0.003(3) -0.010(4) C35B 0.033(4) 0.052(5) 0.042(5) 0.013(4) 0.006(4) 0.001(4) C36B 0.034(4) 0.038(4) 0.038(4) 0.007(3) 0.009(3) 0.000(3) P2A 0.0283(10) 0.0250(10) 0.0438(11) 0.0069(8) 0.0079(8) 0.0035(8) F1A 0.104(7) 0.024(4) 0.219(15) -0.045(6) 0.106(9) -0.023(4) F2A 0.060(5) 0.064(5) 0.105(7) -0.043(5) 0.042(5) -0.033(4) F3A 0.032(3) 0.159(10) 0.029(3) 0.005(4) 0.011(3) 0.006(5) F4A 0.032(3) 0.042(3) 0.037(3) 0.009(3) 0.015(3) 0.006(3) F5A 0.048(4) 0.121(9) 0.052(5) 0.035(5) 0.020(3) 0.028(5) F6A 0.048(4) 0.067(5) 0.080(6) 0.032(4) 0.024(4) 0.035(4) P2B 0.0394(11) 0.0258(10) 0.0434(12) -0.0053(8) 0.0043(9) -0.0002(8) F1B 0.044(3) 0.049(4) 0.050(4) -0.009(3) 0.009(3) -0.014(3) F2B 0.045(4) 0.053(4) 0.073(5) -0.005(3) 0.000(3) -0.024(3) F3B 0.092(6) 0.087(6) 0.057(5) 0.038(4) 0.013(4) -0.012(5) F4B 0.069(5) 0.067(5) 0.080(5) -0.023(4) 0.035(4) 0.023(4) F5B 0.062(4) 0.058(4) 0.043(4) 0.009(3) 0.013(3) -0.003(3) F6B 0.064(4) 0.031(3) 0.098(6) -0.014(3) 0.029(4) 0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1A C1A 1.778(7) . ? P1A C31A 1.787(8) . ? P1A C11A 1.788(7) . ? P1A C21A 1.789(7) . ? C1A H1AA 0.9800 . ? C1A H1AB 0.9800 . ? C1A H1AC 0.9800 . ? C11A C16A 1.392(11) . ? C11A C12A 1.401(11) . ? C12A C13A 1.384(11) . ? C12A H12A 0.9500 . ? C13A C14A 1.374(12) . ? C13A H13A 0.9500 . ? C14A C15A 1.373(13) . ? C14A H14A 0.9500 . ? C15A C16A 1.403(12) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A C26A 1.390(10) . ? C21A C22A 1.403(10) . ? C22A C23A 1.369(11) . ? C22A H22A 0.9500 . ? C23A C24A 1.383(12) . ? C23A H23A 0.9500 . ? C24A C25A 1.369(13) . ? C24A H24A 0.9500 . ? C25A C26A 1.390(12) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? C31A C36A 1.383(11) . ? C31A C32A 1.397(11) . ? C32A C33A 1.367(11) . ? C32A H32A 0.9500 . ? C33A C34A 1.370(12) . ? C33A H33A 0.9500 . ? C34A C35A 1.394(13) . ? C34A H34A 0.9500 . ? C35A C36A 1.382(12) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? P1B C1B 1.789(7) . ? P1B C31B 1.792(7) . ? P1B C21B 1.794(7) . ? P1B C11B 1.796(8) . ? C1B H1BA 0.9800 . ? C1B H1BB 0.9800 . ? C1B H1BC 0.9800 . ? C11B C16B 1.381(11) . ? C11B C12B 1.399(10) . ? C12B C13B 1.382(12) . ? C12B H12B 0.9500 . ? C13B C14B 1.388(12) . ? C13B H13B 0.9500 . ? C14B C15B 1.377(12) . ? C14B H14B 0.9500 . ? C15B C16B 1.403(10) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21B C26B 1.390(10) . ? C21B C22B 1.402(10) . ? C22B C23B 1.382(12) . ? C22B H22B 0.9500 . ? C23B C24B 1.366(14) . ? C23B H23B 0.9500 . ? C24B C25B 1.399(13) . ? C24B H24B 0.9500 . ? C25B C26B 1.379(11) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? C31B C36B 1.392(11) . ? C31B C32B 1.418(11) . ? C32B C33B 1.386(11) . ? C32B H32B 0.9500 . ? C33B C34B 1.373(13) . ? C33B H33B 0.9500 . ? C34B C35B 1.384(13) . ? C34B H34B 0.9500 . ? C35B C36B 1.380(12) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? P2A F1A 1.525(8) . ? P2A F3A 1.536(7) . ? P2A F2A' 1.547(9) . ? P2A F5A' 1.564(8) . ? P2A F4A' 1.573(8) . ? P2A F6A 1.581(7) . ? P2A F4A 1.596(6) . ? P2A F2A 1.610(7) . ? P2A F6A' 1.632(8) . ? P2A F1A' 1.633(9) . ? P2A F3A' 1.633(8) . ? P2A F5A 1.640(7) . ? P2B F3B 1.537(7) . ? P2B F4B 1.559(6) . ? P2B F5B' 1.574(9) . ? P2B F2B 1.580(6) . ? P2B F1B' 1.583(10) . ? P2B F6B' 1.585(9) . ? P2B F1B 1.602(6) . ? P2B F4B' 1.609(9) . ? P2B F2B' 1.614(10) . ? P2B F3B' 1.621(9) . ? P2B F6B 1.634(6) . ? P2B F5B 1.641(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A P1A C31A 109.6(4) . . ? C1A P1A C11A 109.1(4) . . ? C31A P1A C11A 108.4(3) . . ? C1A P1A C21A 110.0(3) . . ? C31A P1A C21A 108.6(3) . . ? C11A P1A C21A 111.2(3) . . ? P1A C1A H1AA 109.5 . . ? P1A C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? P1A C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? C16A C11A C12A 119.7(7) . . ? C16A C11A P1A 122.0(6) . . ? C12A C11A P1A 118.3(6) . . ? C13A C12A C11A 119.7(8) . . ? C13A C12A H12A 120.2 . . ? C11A C12A H12A 120.2 . . ? C14A C13A C12A 120.4(8) . . ? C14A C13A H13A 119.8 . . ? C12A C13A H13A 119.8 . . ? C15A C14A C13A 120.7(8) . . ? C15A C14A H14A 119.6 . . ? C13A C14A H14A 119.6 . . ? C14A C15A C16A 120.0(8) . . ? C14A C15A H15A 120.0 . . ? C16A C15A H15A 120.0 . . ? C11A C16A C15A 119.5(8) . . ? C11A C16A H16A 120.3 . . ? C15A C16A H16A 120.3 . . ? C26A C21A C22A 119.8(7) . . ? C26A C21A P1A 120.0(6) . . ? C22A C21A P1A 120.2(6) . . ? C23A C22A C21A 119.5(7) . . ? C23A C22A H22A 120.2 . . ? C21A C22A H22A 120.2 . . ? C22A C23A C24A 120.9(8) . . ? C22A C23A H23A 119.6 . . ? C24A C23A H23A 119.6 . . ? C25A C24A C23A 119.8(8) . . ? C25A C24A H24A 120.1 . . ? C23A C24A H24A 120.1 . . ? C24A C25A C26A 120.8(8) . . ? C24A C25A H25A 119.6 . . ? C26A C25A H25A 119.6 . . ? C21A C26A C25A 119.2(8) . . ? C21A C26A H26A 120.4 . . ? C25A C26A H26A 120.4 . . ? C36A C31A C32A 119.0(7) . . ? C36A C31A P1A 121.2(6) . . ? C32A C31A P1A 119.6(6) . . ? C33A C32A C31A 119.9(8) . . ? C33A C32A H32A 120.1 . . ? C31A C32A H32A 120.1 . . ? C32A C33A C34A 121.4(8) . . ? C32A C33A H33A 119.3 . . ? C34A C33A H33A 119.3 . . ? C33A C34A C35A 119.2(8) . . ? C33A C34A H34A 120.4 . . ? C35A C34A H34A 120.4 . . ? C36A C35A C34A 119.8(8) . . ? C36A C35A H35A 120.1 . . ? C34A C35A H35A 120.1 . . ? C35A C36A C31A 120.6(8) . . ? C35A C36A H36A 119.7 . . ? C31A C36A H36A 119.7 . . ? C1B P1B C31B 110.2(4) . . ? C1B P1B C21B 110.2(3) . . ? C31B P1B C21B 108.8(3) . . ? C1B P1B C11B 107.7(3) . . ? C31B P1B C11B 109.4(3) . . ? C21B P1B C11B 110.5(3) . . ? P1B C1B H1BA 109.5 . . ? P1B C1B H1BB 109.5 . . ? H1BA C1B H1BB 109.5 . . ? P1B C1B H1BC 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C16B C11B C12B 120.9(7) . . ? C16B C11B P1B 120.2(5) . . ? C12B C11B P1B 118.5(6) . . ? C13B C12B C11B 118.8(8) . . ? C13B C12B H12B 120.6 . . ? C11B C12B H12B 120.6 . . ? C12B C13B C14B 120.8(8) . . ? C12B C13B H13B 119.6 . . ? C14B C13B H13B 119.6 . . ? C15B C14B C13B 120.1(7) . . ? C15B C14B H14B 120.0 . . ? C13B C14B H14B 120.0 . . ? C14B C15B C16B 120.0(8) . . ? C14B C15B H15B 120.0 . . ? C16B C15B H15B 120.0 . . ? C11B C16B C15B 119.3(7) . . ? C11B C16B H16B 120.3 . . ? C15B C16B H16B 120.3 . . ? C26B C21B C22B 118.3(7) . . ? C26B C21B P1B 120.9(5) . . ? C22B C21B P1B 120.6(6) . . ? C23B C22B C21B 120.2(8) . . ? C23B C22B H22B 119.9 . . ? C21B C22B H22B 119.9 . . ? C24B C23B C22B 121.0(8) . . ? C24B C23B H23B 119.5 . . ? C22B C23B H23B 119.5 . . ? C23B C24B C25B 119.6(8) . . ? C23B C24B H24B 120.2 . . ? C25B C24B H24B 120.2 . . ? C26B C25B C24B 119.7(8) . . ? C26B C25B H25B 120.1 . . ? C24B C25B H25B 120.1 . . ? C25B C26B C21B 121.2(8) . . ? C25B C26B H26B 119.4 . . ? C21B C26B H26B 119.4 . . ? C36B C31B C32B 120.0(7) . . ? C36B C31B P1B 119.9(6) . . ? C32B C31B P1B 119.9(6) . . ? C33B C32B C31B 119.1(8) . . ? C33B C32B H32B 120.4 . . ? C31B C32B H32B 120.4 . . ? C34B C33B C32B 120.1(8) . . ? C34B C33B H33B 119.9 . . ? C32B C33B H33B 119.9 . . ? C33B C34B C35B 120.8(8) . . ? C33B C34B H34B 119.6 . . ? C35B C34B H34B 119.6 . . ? C36B C35B C34B 120.6(8) . . ? C36B C35B H35B 119.7 . . ? C34B C35B H35B 119.7 . . ? C35B C36B C31B 119.3(8) . . ? C35B C36B H36B 120.3 . . ? C31B C36B H36B 120.3 . . ? F1A P2A F3A 96.3(6) . . ? F1A P2A F6A 93.5(5) . . ? F3A P2A F6A 92.7(4) . . ? F1A P2A F4A 89.8(5) . . ? F3A P2A F4A 91.9(4) . . ? F6A P2A F4A 174.0(4) . . ? F1A P2A F2A 174.9(6) . . ? F3A P2A F2A 88.6(5) . . ? F6A P2A F2A 87.4(5) . . ? F4A P2A F2A 88.9(4) . . ? F1A P2A F5A 89.8(6) . . ? F3A P2A F5A 173.2(6) . . ? F6A P2A F5A 90.0(4) . . ? F4A P2A F5A 85.0(3) . . ? F2A P2A F5A 85.2(5) . . ? F2A' P2A F5A' 93.2(4) . . ? F2A' P2A F4A' 93.0(4) . . ? F5A' P2A F4A' 92.4(4) . . ? F2A' P2A F6A' 90.4(4) . . ? F5A' P2A F6A' 90.3(4) . . ? F4A' P2A F6A' 175.6(5) . . ? F2A' P2A F1A' 176.1(5) . . ? F5A' P2A F1A' 89.6(4) . . ? F4A' P2A F1A' 89.6(4) . . ? F6A' P2A F1A' 86.9(4) . . ? F2A' P2A F3A' 90.1(4) . . ? F5A' P2A F3A' 175.9(5) . . ? F4A' P2A F3A' 89.8(4) . . ? F6A' P2A F3A' 87.3(4) . . ? F1A' P2A F3A' 86.9(4) . . ? F2B P2B F1B 175.3(4) . . ? F3B P2B F4B 95.3(5) . . ? F3B P2B F2B 93.3(4) . . ? F4B P2B F2B 91.8(4) . . ? F3B P2B F1B 90.9(4) . . ? F4B P2B F1B 90.0(4) . . ? F3B P2B F6B 91.0(5) . . ? F4B P2B F6B 173.4(5) . . ? F2B P2B F6B 89.6(4) . . ? F1B P2B F6B 88.1(4) . . ? F3B P2B F5B 176.5(5) . . ? F4B P2B F5B 87.9(4) . . ? F2B P2B F5B 88.0(4) . . ? F1B P2B F5B 87.6(3) . . ? F6B P2B F5B 85.8(4) . . ? F5B' P2B F1B' 91.5(5) . . ? F5B' P2B F6B' 91.5(5) . . ? F1B' P2B F6B' 91.1(5) . . ? F5B' P2B F4B' 90.4(5) . . ? F1B' P2B F4B' 90.1(5) . . ? F6B' P2B F4B' 177.7(6) . . ? F5B' P2B F2B' 90.4(5) . . ? F1B' P2B F2B' 177.8(6) . . ? F6B' P2B F2B' 89.8(5) . . ? F4B' P2B F2B' 88.9(5) . . ? F5B' P2B F3B' 178.4(6) . . ? F1B' P2B F3B' 89.6(5) . . ? F6B' P2B F3B' 89.6(5) . . ? F4B' P2B F3B' 88.5(5) . . ? F2B' P2B F3B' 88.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A P1A C11A C16A 121.3(7) . . . . ? C31A P1A C11A C16A -119.5(7) . . . . ? C21A P1A C11A C16A -0.2(8) . . . . ? C1A P1A C11A C12A -57.5(7) . . . . ? C31A P1A C11A C12A 61.7(7) . . . . ? C21A P1A C11A C12A -178.9(6) . . . . ? C16A C11A C12A C13A 1.0(12) . . . . ? P1A C11A C12A C13A 179.8(6) . . . . ? C11A C12A C13A C14A -1.2(12) . . . . ? C12A C13A C14A C15A 0.9(13) . . . . ? C13A C14A C15A C16A -0.2(13) . . . . ? C12A C11A C16A C15A -0.3(12) . . . . ? P1A C11A C16A C15A -179.1(7) . . . . ? C14A C15A C16A C11A 0.0(13) . . . . ? C1A P1A C21A C26A 159.6(6) . . . . ? C31A P1A C21A C26A 39.7(7) . . . . ? C11A P1A C21A C26A -79.5(7) . . . . ? C1A P1A C21A C22A -18.4(7) . . . . ? C31A P1A C21A C22A -138.3(6) . . . . ? C11A P1A C21A C22A 102.4(6) . . . . ? C26A C21A C22A C23A 0.4(11) . . . . ? P1A C21A C22A C23A 178.4(6) . . . . ? C21A C22A C23A C24A -0.2(12) . . . . ? C22A C23A C24A C25A 0.4(13) . . . . ? C23A C24A C25A C26A -0.7(13) . . . . ? C22A C21A C26A C25A -0.7(12) . . . . ? P1A C21A C26A C25A -178.7(6) . . . . ? C24A C25A C26A C21A 0.9(13) . . . . ? C1A P1A C31A C36A 144.4(7) . . . . ? C11A P1A C31A C36A 25.5(8) . . . . ? C21A P1A C31A C36A -95.4(7) . . . . ? C1A P1A C31A C32A -39.7(7) . . . . ? C11A P1A C31A C32A -158.7(6) . . . . ? C21A P1A C31A C32A 80.4(7) . . . . ? C36A C31A C32A C33A -2.1(12) . . . . ? P1A C31A C32A C33A -178.0(6) . . . . ? C31A C32A C33A C34A 0.9(12) . . . . ? C32A C33A C34A C35A 0.8(13) . . . . ? C33A C34A C35A C36A -1.4(14) . . . . ? C34A C35A C36A C31A 0.1(15) . . . . ? C32A C31A C36A C35A 1.6(13) . . . . ? P1A C31A C36A C35A 177.4(7) . . . . ? C1B P1B C11B C16B 91.3(6) . . . . ? C31B P1B C11B C16B -148.9(6) . . . . ? C21B P1B C11B C16B -29.2(7) . . . . ? C1B P1B C11B C12B -82.0(6) . . . . ? C31B P1B C11B C12B 37.8(7) . . . . ? C21B P1B C11B C12B 157.5(6) . . . . ? C16B C11B C12B C13B -0.7(11) . . . . ? P1B C11B C12B C13B 172.6(6) . . . . ? C11B C12B C13B C14B 1.4(12) . . . . ? C12B C13B C14B C15B -1.9(12) . . . . ? C13B C14B C15B C16B 1.6(11) . . . . ? C12B C11B C16B C15B 0.4(11) . . . . ? P1B C11B C16B C15B -172.7(6) . . . . ? C14B C15B C16B C11B -0.8(11) . . . . ? C1B P1B C21B C26B -169.8(6) . . . . ? C31B P1B C21B C26B 69.3(7) . . . . ? C11B P1B C21B C26B -50.8(7) . . . . ? C1B P1B C21B C22B 15.6(7) . . . . ? C31B P1B C21B C22B -105.4(6) . . . . ? C11B P1B C21B C22B 134.5(6) . . . . ? C26B C21B C22B C23B 2.5(12) . . . . ? P1B C21B C22B C23B 177.3(7) . . . . ? C21B C22B C23B C24B -2.0(14) . . . . ? C22B C23B C24B C25B 0.4(14) . . . . ? C23B C24B C25B C26B 0.6(13) . . . . ? C24B C25B C26B C21B 0.0(12) . . . . ? C22B C21B C26B C25B -1.5(11) . . . . ? P1B C21B C26B C25B -176.3(6) . . . . ? C1B P1B C31B C36B 171.8(6) . . . . ? C21B P1B C31B C36B -67.2(7) . . . . ? C11B P1B C31B C36B 53.5(7) . . . . ? C1B P1B C31B C32B -13.4(7) . . . . ? C21B P1B C31B C32B 107.5(6) . . . . ? C11B P1B C31B C32B -131.7(6) . . . . ? C36B C31B C32B C33B -0.1(11) . . . . ? P1B C31B C32B C33B -174.8(6) . . . . ? C31B C32B C33B C34B -0.1(12) . . . . ? C32B C33B C34B C35B 0.2(13) . . . . ? C33B C34B C35B C36B -0.1(13) . . . . ? C34B C35B C36B C31B 0.0(12) . . . . ? C32B C31B C36B C35B 0.1(12) . . . . ? P1B C31B C36B C35B 174.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 67.22 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.259 _refine_diff_density_min -0.709 _refine_diff_density_rms 0.137 # Attachment 'Complex_1b.cif' data_110808g_1b _database_code_depnum_ccdc_archive 'CCDC 760637' #TrackingRef 'Complex_1b.cif' # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 P, F6 P' _chemical_formula_sum 'C19 H18 F6 P2' _chemical_formula_weight 422.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4960(5) _cell_length_b 13.6086(6) _cell_length_c 13.6691(11) _cell_angle_alpha 87.766(5) _cell_angle_beta 87.959(5) _cell_angle_gamma 74.793(4) _cell_volume 1881.99(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13054 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 32.5 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method ? _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.289 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_T_max 0.9634 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49476 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 32.47 _reflns_number_total 12509 _reflns_number_gt 9772 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+37.6000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12509 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1447 _refine_ls_R_factor_gt 0.1249 _refine_ls_wR_factor_ref 0.3317 _refine_ls_wR_factor_gt 0.3227 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1A P 0.02590(13) 0.16503(10) 0.85303(10) 0.0152(3) Uani 1 1 d . . . C1A C -0.1111(6) 0.1425(4) 0.9218(4) 0.0209(10) Uani 1 1 d . . . H1AA H -0.0992 0.1506 0.9916 0.031 Uiso 1 1 calc R . . H1AB H -0.1171 0.0730 0.9113 0.031 Uiso 1 1 calc R . . H1AC H -0.1924 0.1913 0.9005 0.031 Uiso 1 1 calc R . . C11A C 0.0052(5) 0.1506(4) 0.7248(4) 0.0158(9) Uani 1 1 d . . . C12A C -0.0886(6) 0.1049(5) 0.6958(5) 0.0251(12) Uani 1 1 d . . . H12A H -0.1397 0.0779 0.7432 0.030 Uiso 1 1 calc R . . C13A C -0.1086(7) 0.0984(6) 0.5958(5) 0.0292(13) Uani 1 1 d . . . H13A H -0.1746 0.0681 0.5751 0.035 Uiso 1 1 calc R . . C14A C -0.0322(7) 0.1363(5) 0.5272(5) 0.0269(12) Uani 1 1 d . . . H14A H -0.0458 0.1323 0.4593 0.032 Uiso 1 1 calc R . . C15A C 0.0650(6) 0.1803(5) 0.5579(5) 0.0241(12) Uani 1 1 d . . . H15A H 0.1177 0.2058 0.5106 0.029 Uiso 1 1 calc R . . C16A C 0.0853(6) 0.1873(5) 0.6571(5) 0.0221(11) Uani 1 1 d . . . H16A H 0.1522 0.2165 0.6782 0.027 Uiso 1 1 calc R . . C21A C 0.0361(5) 0.2929(4) 0.8669(4) 0.0150(9) Uani 1 1 d . . . C22A C -0.0809(6) 0.3708(4) 0.8753(5) 0.0230(11) Uani 1 1 d . . . H22A H -0.1639 0.3552 0.8796 0.028 Uiso 1 1 calc R . . C23A C -0.0740(7) 0.4714(5) 0.8771(6) 0.0324(15) Uani 1 1 d . . . H23A H -0.1529 0.5246 0.8832 0.039 Uiso 1 1 calc R . . C24A C 0.0467(8) 0.4945(5) 0.8702(5) 0.0320(15) Uani 1 1 d . . . H24A H 0.0503 0.5635 0.8717 0.038 Uiso 1 1 calc R . . C25A C 0.1622(7) 0.4178(5) 0.8610(5) 0.0266(12) Uani 1 1 d . . . H25A H 0.2450 0.4338 0.8556 0.032 Uiso 1 1 calc R . . C26A C 0.1564(6) 0.3174(5) 0.8598(4) 0.0211(11) Uani 1 1 d . . . H26A H 0.2358 0.2646 0.8541 0.025 Uiso 1 1 calc R . . C31A C 0.1716(5) 0.0758(4) 0.8965(4) 0.0162(9) Uani 1 1 d . . . C32A C 0.2229(6) 0.0924(4) 0.9859(4) 0.0193(10) Uani 1 1 d . . . H32A H 0.1881 0.1544 1.0185 0.023 Uiso 1 1 calc R . . C33A C 0.3250(6) 0.0172(5) 1.0260(5) 0.0239(11) Uani 1 1 d . . . H33A H 0.3590 0.0270 1.0873 0.029 Uiso 1 1 calc R . . C34A C 0.3779(6) -0.0727(5) 0.9769(5) 0.0255(12) Uani 1 1 d . . . H34A H 0.4483 -0.1239 1.0045 0.031 Uiso 1 1 calc R . . C35A C 0.3275(6) -0.0875(5) 0.8872(5) 0.0246(12) Uani 1 1 d . . . H35A H 0.3641 -0.1488 0.8538 0.030 Uiso 1 1 calc R . . C36A C 0.2249(6) -0.0139(4) 0.8464(4) 0.0197(10) Uani 1 1 d . . . H36A H 0.1910 -0.0241 0.7852 0.024 Uiso 1 1 calc R . . P1B P 0.50286(14) 0.33754(10) 0.34868(11) 0.0154(3) Uani 1 1 d . . . C1B C 0.6344(6) 0.3711(5) 0.4068(5) 0.0217(11) Uani 1 1 d . . . H1BA H 0.6275 0.3589 0.4777 0.033 Uiso 1 1 calc R . . H1BB H 0.6288 0.4433 0.3930 0.033 Uiso 1 1 calc R . . H1BC H 0.7192 0.3294 0.3816 0.033 Uiso 1 1 calc R . . C11B C 0.5148(5) 0.3589(4) 0.2186(4) 0.0169(9) Uani 1 1 d . . . C12B C 0.6274(6) 0.3822(4) 0.1772(4) 0.0217(11) Uani 1 1 d . . . H12B H 0.6928 0.3940 0.2182 0.026 Uiso 1 1 calc R . . C13B C 0.6433(7) 0.3881(5) 0.0765(5) 0.0253(12) Uani 1 1 d . . . H13B H 0.7202 0.4030 0.0480 0.030 Uiso 1 1 calc R . . C14B C 0.5468(7) 0.3721(5) 0.0174(5) 0.0256(12) Uani 1 1 d . . . H14B H 0.5576 0.3765 -0.0518 0.031 Uiso 1 1 calc R . . C15B C 0.4345(7) 0.3498(5) 0.0581(5) 0.0256(12) Uani 1 1 d . . . H15B H 0.3687 0.3391 0.0169 0.031 Uiso 1 1 calc R . . C16B C 0.4181(6) 0.3430(4) 0.1587(5) 0.0216(11) Uani 1 1 d . . . H16B H 0.3413 0.3275 0.1867 0.026 Uiso 1 1 calc R . . C21B C 0.5109(5) 0.2064(4) 0.3705(4) 0.0161(9) Uani 1 1 d . . . C22B C 0.6305(6) 0.1390(4) 0.3982(5) 0.0237(11) Uani 1 1 d . . . H22B H 0.7030 0.1646 0.4138 0.028 Uiso 1 1 calc R . . C23B C 0.6430(7) 0.0352(5) 0.4029(5) 0.0288(13) Uani 1 1 d . . . H23B H 0.7238 -0.0103 0.4225 0.035 Uiso 1 1 calc R . . C24B C 0.5369(8) -0.0028(5) 0.3787(5) 0.0302(14) Uani 1 1 d . . . H24B H 0.5460 -0.0741 0.3809 0.036 Uiso 1 1 calc R . . C25B C 0.4189(7) 0.0637(5) 0.3516(5) 0.0293(13) Uani 1 1 d . . . H25B H 0.3467 0.0381 0.3350 0.035 Uiso 1 1 calc R . . C26B C 0.4057(6) 0.1687(5) 0.3484(5) 0.0229(11) Uani 1 1 d . . . H26B H 0.3239 0.2143 0.3310 0.027 Uiso 1 1 calc R . . C31B C 0.3502(5) 0.4148(4) 0.3974(4) 0.0183(10) Uani 1 1 d . . . C32B C 0.3032(6) 0.3856(4) 0.4882(5) 0.0215(11) Uani 1 1 d . . . H32B H 0.3447 0.3219 0.5186 0.026 Uiso 1 1 calc R . . C33B C 0.1946(6) 0.4518(5) 0.5331(5) 0.0274(13) Uani 1 1 d . . . H33B H 0.1613 0.4334 0.5947 0.033 Uiso 1 1 calc R . . C34B C 0.1349(6) 0.5450(5) 0.4875(5) 0.0272(13) Uani 1 1 d . . . H34B H 0.0610 0.5898 0.5185 0.033 Uiso 1 1 calc R . . C35B C 0.1812(6) 0.5732(5) 0.3982(5) 0.0260(12) Uani 1 1 d . . . H35B H 0.1396 0.6371 0.3680 0.031 Uiso 1 1 calc R . . C36B C 0.2897(6) 0.5075(4) 0.3519(5) 0.0220(11) Uani 1 1 d . . . H36B H 0.3217 0.5262 0.2899 0.026 Uiso 1 1 calc R . . P2A P 0.52613(15) 0.27070(11) 0.73174(12) 0.0194(3) Uani 1 1 d . . . F1A F 0.4667(4) 0.2671(4) 0.8411(3) 0.0401(11) Uani 1 1 d . . . F2A F 0.3968(4) 0.2473(3) 0.6903(3) 0.0291(8) Uani 1 1 d . . . F3A F 0.5860(5) 0.2725(4) 0.6237(3) 0.0438(12) Uani 1 1 d . . . F4A F 0.6550(4) 0.2957(3) 0.7740(3) 0.0272(8) Uani 1 1 d . . . F5A F 0.4570(4) 0.3897(3) 0.7218(4) 0.0428(12) Uani 1 1 d . . . F6A F 0.5954(4) 0.1520(3) 0.7428(4) 0.0391(11) Uani 1 1 d . . . P2B P 0.01472(16) 0.20918(12) 0.23191(12) 0.0217(3) Uani 1 1 d . . . F1B F -0.0716(4) 0.2589(3) 0.1399(3) 0.0349(9) Uani 1 1 d . . . F2B F 0.1366(5) 0.2447(4) 0.1834(3) 0.0392(10) Uani 1 1 d . . . F3B F 0.1031(5) 0.1582(5) 0.3225(4) 0.0518(14) Uani 1 1 d . . . F4B F -0.1086(4) 0.1744(3) 0.2803(3) 0.0322(9) Uani 1 1 d . . . F5B F 0.0579(5) 0.1039(3) 0.1761(4) 0.0445(12) Uani 1 1 d . . . F6B F -0.0326(6) 0.3142(4) 0.2870(4) 0.0466(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1A 0.0136(6) 0.0142(6) 0.0183(6) -0.0002(5) 0.0019(5) -0.0049(5) C1A 0.018(2) 0.020(3) 0.024(3) 0.000(2) 0.004(2) -0.007(2) C11A 0.015(2) 0.011(2) 0.022(2) -0.0009(18) -0.0040(18) -0.0028(17) C12A 0.023(3) 0.026(3) 0.027(3) -0.002(2) 0.001(2) -0.009(2) C13A 0.029(3) 0.034(3) 0.028(3) -0.005(3) -0.001(2) -0.013(3) C14A 0.029(3) 0.025(3) 0.026(3) -0.005(2) -0.002(2) -0.004(2) C15A 0.029(3) 0.019(3) 0.023(3) 0.002(2) 0.005(2) -0.004(2) C16A 0.019(2) 0.022(3) 0.024(3) 0.004(2) 0.005(2) -0.005(2) C21A 0.017(2) 0.012(2) 0.016(2) -0.0021(17) 0.0014(17) -0.0041(17) C22A 0.020(3) 0.017(2) 0.029(3) -0.003(2) -0.004(2) 0.000(2) C23A 0.035(4) 0.017(3) 0.041(4) -0.007(3) -0.008(3) 0.003(2) C24A 0.048(4) 0.016(3) 0.035(4) 0.002(2) -0.011(3) -0.014(3) C25A 0.033(3) 0.018(3) 0.031(3) 0.001(2) -0.002(3) -0.010(2) C26A 0.021(3) 0.021(3) 0.024(3) 0.003(2) 0.000(2) -0.011(2) C31A 0.016(2) 0.014(2) 0.019(2) 0.0013(18) 0.0024(18) -0.0058(18) C32A 0.019(2) 0.018(2) 0.023(3) -0.001(2) 0.001(2) -0.0076(19) C33A 0.022(3) 0.026(3) 0.026(3) 0.005(2) -0.004(2) -0.010(2) C34A 0.018(3) 0.020(3) 0.037(3) 0.006(2) -0.001(2) -0.004(2) C35A 0.024(3) 0.017(2) 0.031(3) 0.000(2) 0.003(2) -0.002(2) C36A 0.023(3) 0.013(2) 0.023(3) -0.0027(19) 0.001(2) -0.0043(19) P1B 0.0146(6) 0.0130(6) 0.0195(6) -0.0014(5) -0.0012(5) -0.0047(5) C1B 0.021(3) 0.022(3) 0.024(3) -0.002(2) -0.004(2) -0.008(2) C11B 0.017(2) 0.010(2) 0.022(2) 0.0002(18) -0.0031(19) -0.0009(17) C12B 0.023(3) 0.021(3) 0.023(3) 0.000(2) -0.002(2) -0.010(2) C13B 0.029(3) 0.025(3) 0.023(3) 0.002(2) -0.001(2) -0.008(2) C14B 0.034(3) 0.020(3) 0.021(3) -0.002(2) 0.001(2) -0.004(2) C15B 0.028(3) 0.026(3) 0.023(3) -0.003(2) -0.006(2) -0.006(2) C16B 0.019(2) 0.019(2) 0.026(3) -0.001(2) -0.004(2) -0.004(2) C21B 0.015(2) 0.012(2) 0.022(2) -0.0007(18) 0.0035(18) -0.0052(17) C22B 0.018(3) 0.017(2) 0.034(3) 0.003(2) 0.001(2) -0.002(2) C23B 0.031(3) 0.018(3) 0.031(3) 0.002(2) 0.002(3) 0.004(2) C24B 0.046(4) 0.014(2) 0.029(3) -0.002(2) 0.007(3) -0.007(3) C25B 0.037(3) 0.022(3) 0.034(3) 0.001(2) -0.005(3) -0.015(3) C26B 0.018(2) 0.021(3) 0.031(3) -0.002(2) 0.000(2) -0.008(2) C31B 0.018(2) 0.015(2) 0.023(3) -0.0033(19) 0.0005(19) -0.0054(19) C32B 0.021(3) 0.019(2) 0.026(3) -0.001(2) -0.004(2) -0.007(2) C33B 0.024(3) 0.031(3) 0.029(3) -0.009(3) 0.006(2) -0.012(2) C34B 0.017(3) 0.024(3) 0.042(4) -0.016(3) 0.001(2) -0.006(2) C35B 0.022(3) 0.016(2) 0.039(3) -0.004(2) -0.003(2) -0.001(2) C36B 0.025(3) 0.016(2) 0.025(3) -0.002(2) -0.003(2) -0.005(2) P2A 0.0190(6) 0.0176(6) 0.0228(7) -0.0018(5) -0.0003(5) -0.0067(5) F1A 0.032(2) 0.070(3) 0.024(2) -0.005(2) -0.0004(17) -0.024(2) F2A 0.0237(18) 0.031(2) 0.035(2) -0.0048(16) -0.0031(15) -0.0115(16) F3A 0.040(3) 0.071(3) 0.024(2) 0.001(2) 0.0024(18) -0.022(2) F4A 0.0239(18) 0.0273(19) 0.034(2) -0.0003(15) -0.0040(15) -0.0121(15) F5A 0.028(2) 0.0193(19) 0.080(4) 0.000(2) -0.012(2) -0.0034(16) F6A 0.029(2) 0.0171(18) 0.072(3) 0.0017(19) -0.011(2) -0.0058(15) P2B 0.0210(7) 0.0230(7) 0.0224(7) -0.0012(6) 0.0014(5) -0.0082(6) F1B 0.039(2) 0.034(2) 0.033(2) 0.0043(17) -0.0073(18) -0.0103(18) F2B 0.039(2) 0.053(3) 0.035(2) 0.001(2) 0.0032(19) -0.030(2) F3B 0.032(2) 0.082(4) 0.041(3) 0.026(3) -0.005(2) -0.017(3) F4B 0.029(2) 0.040(2) 0.033(2) -0.0045(17) 0.0051(16) -0.0194(18) F5B 0.059(3) 0.022(2) 0.049(3) -0.0048(18) 0.026(2) -0.007(2) F6B 0.070(3) 0.034(2) 0.044(3) -0.020(2) 0.017(2) -0.027(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1A C1A 1.777(6) . ? P1A C21A 1.788(5) . ? P1A C31A 1.789(6) . ? P1A C11A 1.799(6) . ? C1A H1AA 0.9800 . ? C1A H1AB 0.9800 . ? C1A H1AC 0.9800 . ? C11A C12A 1.372(8) . ? C11A C16A 1.394(8) . ? C12A C13A 1.399(9) . ? C12A H12A 0.9500 . ? C13A C14A 1.384(10) . ? C13A H13A 0.9500 . ? C14A C15A 1.395(9) . ? C14A H14A 0.9500 . ? C15A C16A 1.390(9) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? C21A C26A 1.387(7) . ? C21A C22A 1.401(8) . ? C22A C23A 1.390(9) . ? C22A H22A 0.9500 . ? C23A C24A 1.383(11) . ? C23A H23A 0.9500 . ? C24A C25A 1.382(10) . ? C24A H24A 0.9500 . ? C25A C26A 1.385(8) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? C31A C36A 1.398(7) . ? C31A C32A 1.401(8) . ? C32A C33A 1.386(8) . ? C32A H32A 0.9500 . ? C33A C34A 1.391(9) . ? C33A H33A 0.9500 . ? C34A C35A 1.395(10) . ? C34A H34A 0.9500 . ? C35A C36A 1.381(8) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? P1B C21B 1.779(5) . ? P1B C1B 1.784(6) . ? P1B C31B 1.792(6) . ? P1B C11B 1.796(6) . ? C1B H1BA 0.9800 . ? C1B H1BB 0.9800 . ? C1B H1BC 0.9800 . ? C11B C16B 1.392(8) . ? C11B C12B 1.397(8) . ? C12B C13B 1.383(9) . ? C12B H12B 0.9500 . ? C13B C14B 1.383(9) . ? C13B H13B 0.9500 . ? C14B C15B 1.386(9) . ? C14B H14B 0.9500 . ? C15B C16B 1.381(9) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? C21B C26B 1.381(8) . ? C21B C22B 1.402(8) . ? C22B C23B 1.383(8) . ? C22B H22B 0.9500 . ? C23B C24B 1.400(10) . ? C23B H23B 0.9500 . ? C24B C25B 1.382(10) . ? C24B H24B 0.9500 . ? C25B C26B 1.397(8) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? C31B C36B 1.390(8) . ? C31B C32B 1.400(8) . ? C32B C33B 1.394(9) . ? C32B H32B 0.9500 . ? C33B C34B 1.392(10) . ? C33B H33B 0.9500 . ? C34B C35B 1.376(10) . ? C34B H34B 0.9500 . ? C35B C36B 1.398(8) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? P2A F3A 1.586(5) . ? P2A F6A 1.591(4) . ? P2A F5A 1.594(4) . ? P2A F2A 1.600(4) . ? P2A F1A 1.603(5) . ? P2A F4A 1.609(4) . ? P2B F6B 1.595(5) . ? P2B F2B 1.597(4) . ? P2B F3B 1.597(5) . ? P2B F1B 1.598(5) . ? P2B F5B 1.600(5) . ? P2B F4B 1.604(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1A P1A C21A 110.6(3) . . ? C1A P1A C31A 107.6(3) . . ? C21A P1A C31A 110.6(3) . . ? C1A P1A C11A 109.9(3) . . ? C21A P1A C11A 106.8(2) . . ? C31A P1A C11A 111.3(3) . . ? P1A C1A H1AA 109.5 . . ? P1A C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? P1A C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? C12A C11A C16A 121.6(6) . . ? C12A C11A P1A 119.8(5) . . ? C16A C11A P1A 118.5(4) . . ? C11A C12A C13A 119.5(6) . . ? C11A C12A H12A 120.2 . . ? C13A C12A H12A 120.2 . . ? C14A C13A C12A 119.8(6) . . ? C14A C13A H13A 120.1 . . ? C12A C13A H13A 120.1 . . ? C13A C14A C15A 119.9(6) . . ? C13A C14A H14A 120.1 . . ? C15A C14A H14A 120.1 . . ? C16A C15A C14A 120.7(6) . . ? C16A C15A H15A 119.7 . . ? C14A C15A H15A 119.7 . . ? C15A C16A C11A 118.4(6) . . ? C15A C16A H16A 120.8 . . ? C11A C16A H16A 120.8 . . ? C26A C21A C22A 119.5(5) . . ? C26A C21A P1A 121.2(4) . . ? C22A C21A P1A 119.0(4) . . ? C23A C22A C21A 119.3(6) . . ? C23A C22A H22A 120.4 . . ? C21A C22A H22A 120.4 . . ? C24A C23A C22A 120.5(6) . . ? C24A C23A H23A 119.7 . . ? C22A C23A H23A 119.7 . . ? C25A C24A C23A 120.3(6) . . ? C25A C24A H24A 119.9 . . ? C23A C24A H24A 119.9 . . ? C24A C25A C26A 119.6(6) . . ? C24A C25A H25A 120.2 . . ? C26A C25A H25A 120.2 . . ? C25A C26A C21A 120.8(6) . . ? C25A C26A H26A 119.6 . . ? C21A C26A H26A 119.6 . . ? C36A C31A C32A 120.8(5) . . ? C36A C31A P1A 119.8(4) . . ? C32A C31A P1A 119.2(4) . . ? C33A C32A C31A 119.3(5) . . ? C33A C32A H32A 120.4 . . ? C31A C32A H32A 120.4 . . ? C32A C33A C34A 120.2(6) . . ? C32A C33A H33A 119.9 . . ? C34A C33A H33A 119.9 . . ? C33A C34A C35A 119.9(6) . . ? C33A C34A H34A 120.0 . . ? C35A C34A H34A 120.0 . . ? C36A C35A C34A 120.7(6) . . ? C36A C35A H35A 119.6 . . ? C34A C35A H35A 119.6 . . ? C35A C36A C31A 119.0(6) . . ? C35A C36A H36A 120.5 . . ? C31A C36A H36A 120.5 . . ? C21B P1B C1B 110.9(3) . . ? C21B P1B C31B 110.0(3) . . ? C1B P1B C31B 107.9(3) . . ? C21B P1B C11B 107.7(3) . . ? C1B P1B C11B 109.9(3) . . ? C31B P1B C11B 110.5(3) . . ? P1B C1B H1BA 109.5 . . ? P1B C1B H1BB 109.5 . . ? H1BA C1B H1BB 109.5 . . ? P1B C1B H1BC 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C16B C11B C12B 120.1(5) . . ? C16B C11B P1B 120.0(4) . . ? C12B C11B P1B 119.7(4) . . ? C13B C12B C11B 119.8(6) . . ? C13B C12B H12B 120.1 . . ? C11B C12B H12B 120.1 . . ? C12B C13B C14B 119.8(6) . . ? C12B C13B H13B 120.1 . . ? C14B C13B H13B 120.1 . . ? C13B C14B C15B 120.6(6) . . ? C13B C14B H14B 119.7 . . ? C15B C14B H14B 119.7 . . ? C16B C15B C14B 120.0(6) . . ? C16B C15B H15B 120.0 . . ? C14B C15B H15B 120.0 . . ? C15B C16B C11B 119.7(6) . . ? C15B C16B H16B 120.2 . . ? C11B C16B H16B 120.2 . . ? C26B C21B C22B 119.7(5) . . ? C26B C21B P1B 120.4(4) . . ? C22B C21B P1B 119.4(4) . . ? C23B C22B C21B 120.0(6) . . ? C23B C22B H22B 120.0 . . ? C21B C22B H22B 120.0 . . ? C22B C23B C24B 120.1(6) . . ? C22B C23B H23B 119.9 . . ? C24B C23B H23B 119.9 . . ? C25B C24B C23B 119.9(6) . . ? C25B C24B H24B 120.1 . . ? C23B C24B H24B 120.1 . . ? C24B C25B C26B 120.0(6) . . ? C24B C25B H25B 120.0 . . ? C26B C25B H25B 120.0 . . ? C21B C26B C25B 120.4(6) . . ? C21B C26B H26B 119.8 . . ? C25B C26B H26B 119.8 . . ? C36B C31B C32B 121.0(5) . . ? C36B C31B P1B 120.2(5) . . ? C32B C31B P1B 118.3(4) . . ? C33B C32B C31B 118.9(6) . . ? C33B C32B H32B 120.6 . . ? C31B C32B H32B 120.6 . . ? C34B C33B C32B 119.9(6) . . ? C34B C33B H33B 120.1 . . ? C32B C33B H33B 120.1 . . ? C35B C34B C33B 121.1(6) . . ? C35B C34B H34B 119.5 . . ? C33B C34B H34B 119.5 . . ? C34B C35B C36B 119.8(6) . . ? C34B C35B H35B 120.1 . . ? C36B C35B H35B 120.1 . . ? C31B C36B C35B 119.4(6) . . ? C31B C36B H36B 120.3 . . ? C35B C36B H36B 120.3 . . ? F3A P2A F6A 90.2(3) . . ? F3A P2A F5A 90.2(3) . . ? F6A P2A F5A 179.4(3) . . ? F3A P2A F2A 90.2(2) . . ? F6A P2A F2A 90.7(2) . . ? F5A P2A F2A 89.6(2) . . ? F3A P2A F1A 179.1(3) . . ? F6A P2A F1A 88.9(3) . . ? F5A P2A F1A 90.6(3) . . ? F2A P2A F1A 89.8(2) . . ? F3A P2A F4A 90.2(2) . . ? F6A P2A F4A 90.0(2) . . ? F5A P2A F4A 89.7(2) . . ? F2A P2A F4A 179.2(2) . . ? F1A P2A F4A 89.8(2) . . ? F6B P2B F2B 90.1(3) . . ? F6B P2B F3B 90.7(3) . . ? F2B P2B F3B 90.2(3) . . ? F6B P2B F1B 90.2(3) . . ? F2B P2B F1B 89.2(3) . . ? F3B P2B F1B 178.9(3) . . ? F6B P2B F5B 178.4(3) . . ? F2B P2B F5B 91.2(3) . . ? F3B P2B F5B 90.3(3) . . ? F1B P2B F5B 88.8(3) . . ? F6B P2B F4B 89.6(3) . . ? F2B P2B F4B 179.5(3) . . ? F3B P2B F4B 90.2(2) . . ? F1B P2B F4B 90.5(2) . . ? F5B P2B F4B 89.1(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A P1A C11A C12A -13.9(6) . . . . ? C21A P1A C11A C12A -134.0(5) . . . . ? C31A P1A C11A C12A 105.2(5) . . . . ? C1A P1A C11A C16A 165.5(4) . . . . ? C21A P1A C11A C16A 45.5(5) . . . . ? C31A P1A C11A C16A -75.4(5) . . . . ? C16A C11A C12A C13A -2.6(9) . . . . ? P1A C11A C12A C13A 176.9(5) . . . . ? C11A C12A C13A C14A 1.2(10) . . . . ? C12A C13A C14A C15A 0.3(10) . . . . ? C13A C14A C15A C16A -0.5(10) . . . . ? C14A C15A C16A C11A -0.9(9) . . . . ? C12A C11A C16A C15A 2.4(9) . . . . ? P1A C11A C16A C15A -177.1(4) . . . . ? C1A P1A C21A C26A 151.0(5) . . . . ? C31A P1A C21A C26A 31.8(5) . . . . ? C11A P1A C21A C26A -89.4(5) . . . . ? C1A P1A C21A C22A -35.4(5) . . . . ? C31A P1A C21A C22A -154.6(5) . . . . ? C11A P1A C21A C22A 84.2(5) . . . . ? C26A C21A C22A C23A -0.5(9) . . . . ? P1A C21A C22A C23A -174.2(5) . . . . ? C21A C22A C23A C24A 0.4(10) . . . . ? C22A C23A C24A C25A 0.1(11) . . . . ? C23A C24A C25A C26A -0.6(11) . . . . ? C24A C25A C26A C21A 0.5(10) . . . . ? C22A C21A C26A C25A 0.0(9) . . . . ? P1A C21A C26A C25A 173.6(5) . . . . ? C1A P1A C31A C36A 97.5(5) . . . . ? C21A P1A C31A C36A -141.5(4) . . . . ? C11A P1A C31A C36A -23.0(5) . . . . ? C1A P1A C31A C32A -76.2(5) . . . . ? C21A P1A C31A C32A 44.7(5) . . . . ? C11A P1A C31A C32A 163.3(4) . . . . ? C36A C31A C32A C33A -2.0(8) . . . . ? P1A C31A C32A C33A 171.6(4) . . . . ? C31A C32A C33A C34A 1.5(9) . . . . ? C32A C33A C34A C35A -0.4(9) . . . . ? C33A C34A C35A C36A -0.2(9) . . . . ? C34A C35A C36A C31A -0.3(9) . . . . ? C32A C31A C36A C35A 1.4(8) . . . . ? P1A C31A C36A C35A -172.2(5) . . . . ? C21B P1B C11B C16B 62.5(5) . . . . ? C1B P1B C11B C16B -176.6(4) . . . . ? C31B P1B C11B C16B -57.6(5) . . . . ? C21B P1B C11B C12B -111.5(5) . . . . ? C1B P1B C11B C12B 9.3(5) . . . . ? C31B P1B C11B C12B 128.4(5) . . . . ? C16B C11B C12B C13B -0.9(9) . . . . ? P1B C11B C12B C13B 173.1(5) . . . . ? C11B C12B C13B C14B 0.9(9) . . . . ? C12B C13B C14B C15B -0.4(10) . . . . ? C13B C14B C15B C16B -0.1(10) . . . . ? C14B C15B C16B C11B 0.1(9) . . . . ? C12B C11B C16B C15B 0.4(8) . . . . ? P1B C11B C16B C15B -173.6(5) . . . . ? C1B P1B C21B C26B 167.7(5) . . . . ? C31B P1B C21B C26B 48.4(6) . . . . ? C11B P1B C21B C26B -72.1(5) . . . . ? C1B P1B C21B C22B -20.6(6) . . . . ? C31B P1B C21B C22B -139.8(5) . . . . ? C11B P1B C21B C22B 99.7(5) . . . . ? C26B C21B C22B C23B 0.3(9) . . . . ? P1B C21B C22B C23B -171.5(5) . . . . ? C21B C22B C23B C24B 0.8(10) . . . . ? C22B C23B C24B C25B -0.9(10) . . . . ? C23B C24B C25B C26B -0.1(10) . . . . ? C22B C21B C26B C25B -1.4(9) . . . . ? P1B C21B C26B C25B 170.4(5) . . . . ? C24B C25B C26B C21B 1.2(10) . . . . ? C21B P1B C31B C36B -147.5(5) . . . . ? C1B P1B C31B C36B 91.4(5) . . . . ? C11B P1B C31B C36B -28.8(5) . . . . ? C21B P1B C31B C32B 40.4(5) . . . . ? C1B P1B C31B C32B -80.6(5) . . . . ? C11B P1B C31B C32B 159.2(4) . . . . ? C36B C31B C32B C33B -0.5(9) . . . . ? P1B C31B C32B C33B 171.5(5) . . . . ? C31B C32B C33B C34B 0.1(9) . . . . ? C32B C33B C34B C35B 0.1(9) . . . . ? C33B C34B C35B C36B 0.2(9) . . . . ? C32B C31B C36B C35B 0.8(9) . . . . ? P1B C31B C36B C35B -171.0(5) . . . . ? C34B C35B C36B C31B -0.6(9) . . . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.981 _refine_diff_density_min -0.896 _refine_diff_density_rms 0.183 # Attachment 'Complex_2.cif' data_160808l _database_code_depnum_ccdc_archive 'CCDC 760638' #TrackingRef 'Complex_2.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 P, C2 N3' _chemical_formula_sum 'C26 H20 N3 P' _chemical_formula_weight 405.42 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I -4' _symmetry_space_group_name_Hall 'I -4' _symmetry_int_tables_number 82 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 16.946(2) _cell_length_b 16.946 _cell_length_c 14.303(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 4107.3(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20612 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 32.26 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method ? _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96978 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 54064 _diffrn_reflns_av_R_equivalents 0.0634 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 32.34 _reflns_number_total 7020 _reflns_number_gt 5879 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(7) _refine_ls_number_reflns 7020 _refine_ls_number_parameters 270 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.0000 0.0000 0.0000 0.01202(11) Uani 1 4 d S . . C11 C 0.08462(7) -0.00876(7) 0.07384(9) 0.0145(2) Uani 1 1 d . . . C12 C 0.12021(7) 0.05943(7) 0.10833(9) 0.0174(2) Uani 1 1 d . . . H12 H 0.1031 0.1098 0.0875 0.021 Uiso 1 1 calc R . . C13 C 0.18062(8) 0.05349(8) 0.17309(10) 0.0202(3) Uani 1 1 d . . . H13 H 0.2049 0.0999 0.1968 0.024 Uiso 1 1 calc R . . C14 C 0.20565(8) -0.01989(8) 0.20331(10) 0.0232(3) Uani 1 1 d . . . H14 H 0.2476 -0.0236 0.2471 0.028 Uiso 1 1 calc R . . C15 C 0.17000(8) -0.08805(8) 0.17027(11) 0.0250(3) Uani 1 1 d . . . H15 H 0.1874 -0.1382 0.1914 0.030 Uiso 1 1 calc R . . C16 C 0.10888(8) -0.08274(8) 0.10631(10) 0.0203(3) Uani 1 1 d . . . H16 H 0.0835 -0.1292 0.0846 0.024 Uiso 1 1 calc R . . P2 P 0.0000 0.0000 0.5000 0.01332(12) Uani 1 4 d S . . C21 C -0.00847(7) 0.08489(7) 0.42615(9) 0.0152(2) Uani 1 1 d . . . C22 C 0.05446(8) 0.10307(8) 0.36650(10) 0.0203(3) Uani 1 1 d . . . H22 H 0.1009 0.0717 0.3673 0.024 Uiso 1 1 calc R . . C23 C 0.04906(8) 0.16667(8) 0.30644(10) 0.0226(3) Uani 1 1 d . . . H23 H 0.0921 0.1798 0.2669 0.027 Uiso 1 1 calc R . . C24 C -0.01958(8) 0.21121(7) 0.30414(10) 0.0213(3) Uani 1 1 d . . . H24 H -0.0236 0.2545 0.2621 0.026 Uiso 1 1 calc R . . C25 C -0.08203(8) 0.19344(8) 0.36207(11) 0.0246(3) Uani 1 1 d . . . H25 H -0.1289 0.2241 0.3596 0.029 Uiso 1 1 calc R . . C26 C -0.07647(8) 0.13067(8) 0.42411(10) 0.0209(3) Uani 1 1 d . . . H26 H -0.1191 0.1191 0.4651 0.025 Uiso 1 1 calc R . . P3 P 0.5000 0.0000 0.2500 0.01212(11) Uani 1 4 d S . . C31 C 0.45942(7) 0.07613(7) 0.17768(9) 0.0144(2) Uani 1 1 d . . . C32 C 0.38739(7) 0.11149(7) 0.19939(9) 0.0164(2) Uani 1 1 d . . . H32 H 0.3572 0.0931 0.2509 0.020 Uiso 1 1 calc R . . C33 C 0.36002(8) 0.17383(7) 0.14517(10) 0.0204(3) Uani 1 1 d . . . H33 H 0.3109 0.1980 0.1594 0.024 Uiso 1 1 calc R . . C34 C 0.40436(8) 0.20048(7) 0.07062(10) 0.0213(3) Uani 1 1 d . . . H34 H 0.3855 0.2432 0.0338 0.026 Uiso 1 1 calc R . . C35 C 0.47598(8) 0.16583(8) 0.04882(10) 0.0213(3) Uani 1 1 d . . . H35 H 0.5061 0.1849 -0.0024 0.026 Uiso 1 1 calc R . . C36 C 0.50373(7) 0.10337(7) 0.10169(9) 0.0171(2) Uani 1 1 d . . . H36 H 0.5526 0.0791 0.0865 0.021 Uiso 1 1 calc R . . P4 P 0.5000 0.0000 0.7500 0.01217(11) Uani 1 4 d S . . C41 C 0.42532(7) 0.04430(7) 0.82143(9) 0.0138(2) Uani 1 1 d . . . C42 C 0.39203(7) 0.11672(7) 0.79611(9) 0.0161(2) Uani 1 1 d . . . H42 H 0.4116 0.1445 0.7433 0.019 Uiso 1 1 calc R . . C43 C 0.33038(7) 0.14791(8) 0.84807(10) 0.0191(3) Uani 1 1 d . . . H43 H 0.3080 0.1973 0.8313 0.023 Uiso 1 1 calc R . . C44 C 0.30148(7) 0.10684(8) 0.92459(10) 0.0197(3) Uani 1 1 d . . . H44 H 0.2592 0.1283 0.9600 0.024 Uiso 1 1 calc R . . C45 C 0.33376(8) 0.03471(8) 0.94994(9) 0.0189(3) Uani 1 1 d . . . H45 H 0.3132 0.0068 1.0021 0.023 Uiso 1 1 calc R . . C46 C 0.39599(7) 0.00333(7) 0.89917(9) 0.0164(2) Uani 1 1 d . . . H46 H 0.4187 -0.0457 0.9170 0.020 Uiso 1 1 calc R . . N1 N 0.24629(7) 0.16305(8) 0.36131(10) 0.0296(3) Uani 1 1 d . . . C1 C 0.29085(8) 0.17045(7) 0.42128(10) 0.0203(3) Uani 1 1 d . . . N2 N 0.33705(7) 0.25281(7) 0.62727(10) 0.0270(3) Uani 1 1 d . . . C2 C 0.33832(7) 0.21738(7) 0.55845(10) 0.0190(3) Uani 1 1 d . . . N3 N 0.34693(7) 0.17281(8) 0.48439(9) 0.0304(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01087(16) 0.01087(16) 0.0143(3) 0.000 0.000 0.000 C11 0.0115(5) 0.0159(5) 0.0162(6) 0.0006(5) -0.0011(4) 0.0019(4) C12 0.0165(6) 0.0144(6) 0.0212(7) -0.0002(5) -0.0017(5) 0.0007(4) C13 0.0169(6) 0.0220(6) 0.0217(7) -0.0020(5) -0.0027(5) -0.0016(5) C14 0.0173(6) 0.0290(7) 0.0233(7) 0.0016(6) -0.0063(5) 0.0029(5) C15 0.0256(7) 0.0208(6) 0.0287(8) 0.0065(6) -0.0061(6) 0.0056(5) C16 0.0229(6) 0.0150(6) 0.0230(7) 0.0009(5) -0.0037(5) -0.0004(5) P2 0.01207(16) 0.01207(16) 0.0158(3) 0.000 0.000 0.000 C21 0.0155(6) 0.0129(5) 0.0172(6) 0.0013(5) -0.0019(5) 0.0003(4) C22 0.0180(6) 0.0200(6) 0.0230(7) 0.0037(5) 0.0054(5) 0.0045(5) C23 0.0216(6) 0.0232(7) 0.0229(7) 0.0038(5) 0.0038(5) -0.0005(5) C24 0.0259(7) 0.0152(6) 0.0228(7) 0.0031(5) -0.0048(5) 0.0004(5) C25 0.0208(6) 0.0209(6) 0.0319(8) 0.0033(6) -0.0034(6) 0.0076(5) C26 0.0153(6) 0.0213(6) 0.0261(7) 0.0035(5) 0.0022(5) 0.0022(5) P3 0.01091(16) 0.01091(16) 0.0145(3) 0.000 0.000 0.000 C31 0.0161(6) 0.0107(5) 0.0163(6) 0.0006(4) -0.0041(5) -0.0008(4) C32 0.0156(6) 0.0138(6) 0.0196(7) -0.0004(5) -0.0020(5) -0.0007(4) C33 0.0189(6) 0.0149(6) 0.0272(7) -0.0017(5) -0.0079(5) 0.0023(5) C34 0.0266(7) 0.0117(5) 0.0256(7) 0.0014(5) -0.0110(6) -0.0022(5) C35 0.0267(7) 0.0177(6) 0.0195(7) 0.0032(5) -0.0026(5) -0.0065(5) C36 0.0159(6) 0.0168(6) 0.0187(6) -0.0006(5) -0.0003(5) -0.0019(5) P4 0.01099(16) 0.01099(16) 0.0145(3) 0.000 0.000 0.000 C41 0.0117(5) 0.0132(5) 0.0165(6) -0.0024(4) 0.0011(4) 0.0000(4) C42 0.0149(6) 0.0145(6) 0.0190(7) -0.0004(5) -0.0013(5) -0.0001(4) C43 0.0148(6) 0.0175(6) 0.0249(7) -0.0034(5) -0.0025(5) 0.0029(5) C44 0.0131(6) 0.0217(6) 0.0243(7) -0.0086(5) 0.0007(5) -0.0002(5) C45 0.0176(6) 0.0199(6) 0.0193(7) -0.0034(5) 0.0024(5) -0.0036(5) C46 0.0169(6) 0.0145(5) 0.0178(6) -0.0006(5) 0.0000(5) -0.0002(4) N1 0.0280(6) 0.0304(7) 0.0303(7) -0.0057(5) -0.0081(6) 0.0080(5) C1 0.0198(6) 0.0182(6) 0.0231(7) -0.0024(5) 0.0028(5) 0.0042(5) N2 0.0301(7) 0.0216(6) 0.0293(7) -0.0036(5) -0.0031(5) 0.0012(5) C2 0.0161(6) 0.0148(6) 0.0260(7) 0.0017(5) -0.0032(5) 0.0012(5) N3 0.0233(6) 0.0371(7) 0.0310(7) -0.0139(6) -0.0086(5) 0.0122(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C11 1.7871(12) . ? P1 C11 1.7871(12) 4 ? P1 C11 1.7872(12) 2 ? P1 C11 1.7872(12) 3 ? C11 C12 1.3937(17) . ? C11 C16 1.3987(17) . ? C12 C13 1.3843(18) . ? C12 H12 0.9500 . ? C13 C14 1.3831(19) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.3848(19) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? P2 C21 1.7904(12) . ? P2 C21 1.7904(12) 4_556 ? P2 C21 1.7905(12) 3_556 ? P2 C21 1.7905(12) 2 ? C21 C26 1.3894(17) . ? C21 C22 1.4002(18) . ? C22 C23 1.3812(18) . ? C22 H22 0.9500 . ? C23 C24 1.3871(19) . ? C23 H23 0.9500 . ? C24 C25 1.377(2) . ? C24 H24 0.9500 . ? C25 C26 1.3884(19) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? P3 C31 1.7908(12) 7 ? P3 C31 1.7909(12) 8_545 ? P3 C31 1.7909(12) 2_655 ? P3 C31 1.7909(12) . ? C31 C32 1.3948(17) . ? C31 C36 1.3993(18) . ? C32 C33 1.3902(18) . ? C32 H32 0.9500 . ? C33 C34 1.381(2) . ? C33 H33 0.9500 . ? C34 C35 1.3837(19) . ? C34 H34 0.9500 . ? C35 C36 1.3833(18) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? P4 C41 1.7914(12) 7_556 ? P4 C41 1.7914(12) . ? P4 C41 1.7915(12) 2_655 ? P4 C41 1.7915(12) 8_546 ? C41 C42 1.3984(17) . ? C41 C46 1.4019(17) . ? C42 C43 1.3867(18) . ? C42 H42 0.9500 . ? C43 C44 1.386(2) . ? C43 H43 0.9500 . ? C44 C45 1.3874(18) . ? C44 H44 0.9500 . ? C45 C46 1.3864(18) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? N1 C1 1.1497(18) . ? C1 N3 1.3112(18) . ? N2 C2 1.1532(18) . ? C2 N3 1.3091(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 P1 C11 110.44(4) . 4 ? C11 P1 C11 107.55(8) . 2 ? C11 P1 C11 110.44(4) 4 2 ? C11 P1 C11 110.44(4) . 3 ? C11 P1 C11 107.55(8) 4 3 ? C11 P1 C11 110.44(4) 2 3 ? C12 C11 C16 119.90(11) . . ? C12 C11 P1 119.17(9) . . ? C16 C11 P1 120.43(9) . . ? C13 C12 C11 119.77(12) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.09(12) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.58(12) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C16 C15 C14 119.80(12) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 119.82(12) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? C21 P2 C21 110.37(4) . 4_556 ? C21 P2 C21 110.37(4) . 3_556 ? C21 P2 C21 107.70(8) 4_556 3_556 ? C21 P2 C21 107.70(8) . 2 ? C21 P2 C21 110.36(4) 4_556 2 ? C21 P2 C21 110.36(4) 3_556 2 ? C26 C21 C22 119.74(11) . . ? C26 C21 P2 121.84(10) . . ? C22 C21 P2 118.37(9) . . ? C23 C22 C21 120.01(12) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C22 C23 C24 119.67(13) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C25 C24 C23 120.73(12) . . ? C25 C24 H24 119.6 . . ? C23 C24 H24 119.6 . . ? C24 C25 C26 120.00(12) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.83(13) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C31 P3 C31 109.44(8) 7 8_545 ? C31 P3 C31 109.49(4) 7 2_655 ? C31 P3 C31 109.49(4) 8_545 2_655 ? C31 P3 C31 109.49(4) 7 . ? C31 P3 C31 109.49(4) 8_545 . ? C31 P3 C31 109.44(8) 2_655 . ? C32 C31 C36 120.06(11) . . ? C32 C31 P3 121.12(10) . . ? C36 C31 P3 118.70(9) . . ? C33 C32 C31 119.62(12) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C34 C33 C32 119.86(12) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C33 C34 C35 120.84(12) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C36 C35 C34 119.99(13) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C31 119.64(12) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C41 P4 C41 108.99(4) 7_556 . ? C41 P4 C41 108.98(4) 7_556 2_655 ? C41 P4 C41 110.45(8) . 2_655 ? C41 P4 C41 110.45(8) 7_556 8_546 ? C41 P4 C41 108.98(4) . 8_546 ? C41 P4 C41 108.98(4) 2_655 8_546 ? C42 C41 C46 119.81(11) . . ? C42 C41 P4 120.33(9) . . ? C46 C41 P4 119.69(9) . . ? C43 C42 C41 119.96(12) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C44 C43 C42 119.87(12) . . ? C44 C43 H43 120.1 . . ? C42 C43 H43 120.1 . . ? C43 C44 C45 120.61(12) . . ? C43 C44 H44 119.7 . . ? C45 C44 H44 119.7 . . ? C46 C45 C44 120.06(13) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C41 119.67(12) . . ? C45 C46 H46 120.2 . . ? C41 C46 H46 120.2 . . ? N1 C1 N3 173.19(15) . . ? N2 C2 N3 173.28(15) . . ? C2 N3 C1 119.60(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 C11 C12 35.95(8) 4 . . . ? C11 P1 C11 C12 -84.63(10) 2 . . . ? C11 P1 C11 C12 154.79(12) 3 . . . ? C11 P1 C11 C16 -152.12(13) 4 . . . ? C11 P1 C11 C16 87.30(11) 2 . . . ? C11 P1 C11 C16 -33.28(9) 3 . . . ? C16 C11 C12 C13 1.42(19) . . . . ? P1 C11 C12 C13 173.39(10) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C12 C13 C14 C15 -0.9(2) . . . . ? C13 C14 C15 C16 0.1(2) . . . . ? C14 C15 C16 C11 1.4(2) . . . . ? C12 C11 C16 C15 -2.2(2) . . . . ? P1 C11 C16 C15 -174.06(11) . . . . ? C21 P2 C21 C26 -5.51(11) 4_556 . . . ? C21 P2 C21 C26 -124.44(14) 3_556 . . . ? C21 P2 C21 C26 115.03(12) 2 . . . ? C21 P2 C21 C22 177.06(12) 4_556 . . . ? C21 P2 C21 C22 58.13(8) 3_556 . . . ? C21 P2 C21 C22 -62.41(10) 2 . . . ? C26 C21 C22 C23 0.5(2) . . . . ? P2 C21 C22 C23 177.99(11) . . . . ? C21 C22 C23 C24 -1.4(2) . . . . ? C22 C23 C24 C25 0.9(2) . . . . ? C23 C24 C25 C26 0.5(2) . . . . ? C24 C25 C26 C21 -1.4(2) . . . . ? C22 C21 C26 C25 0.9(2) . . . . ? P2 C21 C26 C25 -176.50(11) . . . . ? C31 P3 C31 C32 -101.76(13) 7 . . . ? C31 P3 C31 C32 18.22(11) 8_545 . . . ? C31 P3 C31 C32 138.23(12) 2_655 . . . ? C31 P3 C31 C36 74.23(7) 7 . . . ? C31 P3 C31 C36 -165.79(10) 8_545 . . . ? C31 P3 C31 C36 -45.78(8) 2_655 . . . ? C36 C31 C32 C33 -0.02(18) . . . . ? P3 C31 C32 C33 175.91(9) . . . . ? C31 C32 C33 C34 -0.27(18) . . . . ? C32 C33 C34 C35 0.10(19) . . . . ? C33 C34 C35 C36 0.38(19) . . . . ? C34 C35 C36 C31 -0.67(19) . . . . ? C32 C31 C36 C35 0.49(18) . . . . ? P3 C31 C36 C35 -175.54(10) . . . . ? C41 P4 C41 C42 20.80(11) 7_556 . . . ? C41 P4 C41 C42 140.50(12) 2_655 . . . ? C41 P4 C41 C42 -99.80(13) 8_546 . . . ? C41 P4 C41 C46 -164.00(10) 7_556 . . . ? C41 P4 C41 C46 -44.30(9) 2_655 . . . ? C41 P4 C41 C46 75.39(7) 8_546 . . . ? C46 C41 C42 C43 0.23(19) . . . . ? P4 C41 C42 C43 175.42(10) . . . . ? C41 C42 C43 C44 -0.52(19) . . . . ? C42 C43 C44 C45 0.11(19) . . . . ? C43 C44 C45 C46 0.61(19) . . . . ? C44 C45 C46 C41 -0.90(19) . . . . ? C42 C41 C46 C45 0.49(18) . . . . ? P4 C41 C46 C45 -174.73(10) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.397 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.054 # Attachment 'Complex_3.cif' data_260708b _database_code_depnum_ccdc_archive 'CCDC 760639' #TrackingRef 'Complex_3.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 P, C N S' _chemical_formula_sum 'C26 H22 N P S' _chemical_formula_weight 411.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9268(1) _cell_length_b 12.2301(1) _cell_length_c 13.3369(1) _cell_angle_alpha 90.0 _cell_angle_beta 91.491(1) _cell_angle_gamma 90.0 _cell_volume 2107.80(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 26592 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 32.51 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method ? _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9624 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 64934 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 32.60 _reflns_number_total 7451 _reflns_number_gt 5667 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+1.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7451 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1434 _refine_ls_wR_factor_gt 0.1374 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.41139(3) 0.18839(3) 0.27520(3) 0.01392(9) Uani 1 1 d . . . C10 C 0.44471(12) 0.20119(12) 0.40739(11) 0.0167(3) Uani 1 1 d . . . H10A H 0.4324 0.1300 0.4403 0.020 Uiso 1 1 calc R . . H10B H 0.5195 0.2175 0.4146 0.020 Uiso 1 1 calc R . . C11 C 0.38479(11) 0.28904(12) 0.46211(11) 0.0166(3) Uani 1 1 d . . . C12 C 0.31700(12) 0.25689(13) 0.53552(12) 0.0212(3) Uani 1 1 d . . . H12 H 0.3060 0.1812 0.5474 0.025 Uiso 1 1 calc R . . C13 C 0.26504(14) 0.33376(15) 0.59185(13) 0.0265(3) Uani 1 1 d . . . H13 H 0.2202 0.3106 0.6430 0.032 Uiso 1 1 calc R . . C14 C 0.27868(13) 0.44488(15) 0.57338(13) 0.0248(3) Uani 1 1 d . . . H14 H 0.2431 0.4975 0.6119 0.030 Uiso 1 1 calc R . . C15 C 0.34393(13) 0.47843(14) 0.49909(12) 0.0233(3) Uani 1 1 d . . . H15 H 0.3524 0.5541 0.4855 0.028 Uiso 1 1 calc R . . C16 C 0.39756(13) 0.40056(13) 0.44383(12) 0.0227(3) Uani 1 1 d . . . H16 H 0.4432 0.4238 0.3933 0.027 Uiso 1 1 calc R . . C21 C 0.47641(11) 0.28880(12) 0.20144(11) 0.0157(3) Uani 1 1 d . . . C22 C 0.45312(12) 0.29260(12) 0.09862(11) 0.0184(3) Uani 1 1 d . . . H22 H 0.3975 0.2505 0.0711 0.022 Uiso 1 1 calc R . . C23 C 0.51136(13) 0.35795(13) 0.03701(12) 0.0213(3) Uani 1 1 d . . . H23 H 0.4953 0.3608 -0.0329 0.026 Uiso 1 1 calc R . . C24 C 0.59322(12) 0.41957(13) 0.07648(13) 0.0215(3) Uani 1 1 d . . . H24 H 0.6335 0.4634 0.0335 0.026 Uiso 1 1 calc R . . C25 C 0.61598(11) 0.41688(13) 0.17854(12) 0.0195(3) Uani 1 1 d . . . H25 H 0.6708 0.4604 0.2057 0.023 Uiso 1 1 calc R . . C26 C 0.55876(11) 0.35060(12) 0.24136(11) 0.0175(3) Uani 1 1 d . . . H26 H 0.5756 0.3473 0.3111 0.021 Uiso 1 1 calc R . . C31 C 0.45550(11) 0.05811(12) 0.23063(11) 0.0158(3) Uani 1 1 d . . . C32 C 0.54372(12) 0.00906(13) 0.27301(12) 0.0198(3) Uani 1 1 d . . . H32 H 0.5768 0.0396 0.3310 0.024 Uiso 1 1 calc R . . C33 C 0.58288(12) -0.08562(13) 0.22907(12) 0.0206(3) Uani 1 1 d . . . H33 H 0.6426 -0.1201 0.2575 0.025 Uiso 1 1 calc R . . C34 C 0.53464(12) -0.12920(13) 0.14424(12) 0.0209(3) Uani 1 1 d . . . H34 H 0.5624 -0.1925 0.1137 0.025 Uiso 1 1 calc R . . C35 C 0.44627(14) -0.08115(14) 0.10363(12) 0.0245(3) Uani 1 1 d . . . H35 H 0.4128 -0.1126 0.0463 0.029 Uiso 1 1 calc R . . C36 C 0.40634(13) 0.01246(13) 0.14611(12) 0.0219(3) Uani 1 1 d . . . H36 H 0.3458 0.0455 0.1179 0.026 Uiso 1 1 calc R . . C41 C 0.27314(11) 0.19124(12) 0.25489(10) 0.0150(3) Uani 1 1 d . . . C42 C 0.21863(12) 0.10471(13) 0.29772(11) 0.0190(3) Uani 1 1 d . . . H42 H 0.2536 0.0533 0.3398 0.023 Uiso 1 1 calc R . . C43 C 0.11307(12) 0.09480(13) 0.27815(12) 0.0212(3) Uani 1 1 d . . . H43 H 0.0756 0.0365 0.3072 0.025 Uiso 1 1 calc R . . C44 C 0.06207(12) 0.16989(14) 0.21628(13) 0.0233(3) Uani 1 1 d . . . H44 H -0.0099 0.1617 0.2018 0.028 Uiso 1 1 calc R . . C45 C 0.11588(12) 0.25682(14) 0.17558(12) 0.0221(3) Uani 1 1 d . . . H45 H 0.0804 0.3085 0.1341 0.027 Uiso 1 1 calc R . . C46 C 0.22152(12) 0.26845(12) 0.19533(11) 0.0186(3) Uani 1 1 d . . . H46 H 0.2581 0.3286 0.1684 0.022 Uiso 1 1 calc R . . S1 S 0.25742(3) 0.78822(4) 0.59828(4) 0.02944(12) Uani 1 1 d . . . C1 C 0.29749(12) 0.89265(13) 0.53241(11) 0.0184(3) Uani 1 1 d . . . N1 N 0.32806(12) 0.96682(12) 0.48694(11) 0.0264(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01428(16) 0.01397(17) 0.01353(16) 0.00035(12) 0.00080(12) -0.00061(12) C10 0.0183(6) 0.0173(6) 0.0145(6) 0.0006(5) 0.0002(5) 0.0004(5) C11 0.0162(6) 0.0188(6) 0.0148(6) -0.0030(5) 0.0006(5) -0.0015(5) C12 0.0208(7) 0.0205(7) 0.0224(7) -0.0009(5) 0.0040(6) -0.0023(6) C13 0.0261(8) 0.0316(9) 0.0220(7) -0.0037(6) 0.0083(6) -0.0020(7) C14 0.0220(7) 0.0277(8) 0.0250(8) -0.0098(6) 0.0028(6) 0.0027(6) C15 0.0262(8) 0.0183(7) 0.0252(8) -0.0032(6) -0.0009(6) 0.0006(6) C16 0.0264(8) 0.0210(7) 0.0211(7) -0.0021(6) 0.0058(6) -0.0027(6) C21 0.0146(6) 0.0151(6) 0.0174(6) 0.0038(5) 0.0006(5) -0.0009(5) C22 0.0194(7) 0.0175(6) 0.0183(6) 0.0024(5) 0.0001(5) -0.0022(5) C23 0.0241(7) 0.0206(7) 0.0192(7) 0.0019(5) 0.0033(6) -0.0003(6) C24 0.0182(7) 0.0197(7) 0.0268(8) 0.0040(6) 0.0068(6) 0.0004(5) C25 0.0126(6) 0.0184(7) 0.0276(8) 0.0038(5) 0.0007(5) -0.0012(5) C26 0.0137(6) 0.0180(6) 0.0207(7) 0.0037(5) -0.0013(5) -0.0008(5) C31 0.0162(6) 0.0148(6) 0.0167(6) -0.0015(5) 0.0037(5) -0.0013(5) C32 0.0185(7) 0.0202(7) 0.0206(7) -0.0028(5) -0.0013(5) -0.0032(5) C33 0.0162(6) 0.0194(7) 0.0262(8) 0.0005(6) -0.0009(5) 0.0009(5) C34 0.0212(7) 0.0178(7) 0.0240(7) -0.0047(5) 0.0053(6) 0.0021(5) C35 0.0282(8) 0.0259(8) 0.0193(7) -0.0054(6) -0.0025(6) 0.0033(6) C36 0.0216(7) 0.0215(7) 0.0224(7) -0.0025(6) -0.0023(6) 0.0039(6) C41 0.0147(6) 0.0160(6) 0.0142(6) -0.0003(5) -0.0002(5) -0.0019(5) C42 0.0197(7) 0.0186(7) 0.0187(6) 0.0035(5) 0.0009(5) -0.0033(5) C43 0.0187(7) 0.0218(7) 0.0232(7) -0.0001(6) 0.0051(6) -0.0041(6) C44 0.0145(6) 0.0276(8) 0.0280(8) -0.0031(6) 0.0030(6) 0.0013(6) C45 0.0182(7) 0.0247(8) 0.0235(7) 0.0034(6) 0.0019(6) 0.0065(6) C46 0.0200(7) 0.0168(6) 0.0190(7) 0.0022(5) 0.0024(5) 0.0008(5) S1 0.0220(2) 0.0339(2) 0.0321(2) 0.01477(18) -0.00582(16) -0.00831(16) C1 0.0172(6) 0.0193(7) 0.0184(6) -0.0015(5) -0.0054(5) 0.0026(5) N1 0.0331(8) 0.0201(7) 0.0259(7) 0.0032(5) -0.0052(6) -0.0004(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.7958(14) . ? P1 C31 1.7986(15) . ? P1 C41 1.8009(15) . ? P1 C10 1.8107(15) . ? C10 C11 1.522(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.388(2) . ? C11 C16 1.396(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9500 . ? C13 C14 1.393(3) . ? C13 H13 0.9500 . ? C14 C15 1.380(2) . ? C14 H14 0.9500 . ? C15 C16 1.399(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.397(2) . ? C21 C26 1.399(2) . ? C22 C23 1.383(2) . ? C22 H22 0.9500 . ? C23 C24 1.391(2) . ? C23 H23 0.9500 . ? C24 C25 1.385(2) . ? C24 H24 0.9500 . ? C25 C26 1.392(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.395(2) . ? C31 C36 1.396(2) . ? C32 C33 1.398(2) . ? C32 H32 0.9500 . ? C33 C34 1.384(2) . ? C33 H33 0.9500 . ? C34 C35 1.383(2) . ? C34 H34 0.9500 . ? C35 C36 1.383(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.393(2) . ? C41 C42 1.401(2) . ? C42 C43 1.388(2) . ? C42 H42 0.9500 . ? C43 C44 1.389(2) . ? C43 H43 0.9500 . ? C44 C45 1.389(2) . ? C44 H44 0.9500 . ? C45 C46 1.391(2) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? S1 C1 1.6417(16) . ? C1 N1 1.166(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C31 105.53(7) . . ? C21 P1 C41 112.40(7) . . ? C31 P1 C41 106.81(7) . . ? C21 P1 C10 111.81(7) . . ? C31 P1 C10 109.21(7) . . ? C41 P1 C10 110.78(7) . . ? C11 C10 P1 114.63(10) . . ? C11 C10 H10A 108.6 . . ? P1 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? P1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C16 118.67(14) . . ? C12 C11 C10 118.48(13) . . ? C16 C11 C10 122.82(13) . . ? C13 C12 C11 120.90(15) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.99(15) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C15 C14 C13 119.96(15) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 119.75(15) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 120.70(15) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C22 C21 C26 119.85(13) . . ? C22 C21 P1 117.94(11) . . ? C26 C21 P1 121.54(11) . . ? C23 C22 C21 119.71(14) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.58(15) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C25 C24 C23 119.92(14) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.16(14) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 119.76(14) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C32 C31 C36 120.35(14) . . ? C32 C31 P1 120.66(11) . . ? C36 C31 P1 118.66(11) . . ? C31 C32 C33 119.16(14) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C34 C33 C32 120.07(14) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C35 C34 C33 120.44(14) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 120.30(15) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C31 119.66(15) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C46 C41 C42 120.39(13) . . ? C46 C41 P1 123.90(11) . . ? C42 C41 P1 115.57(11) . . ? C43 C42 C41 119.45(14) . . ? C43 C42 H42 120.3 . . ? C41 C42 H42 120.3 . . ? C42 C43 C44 120.20(14) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C43 C44 C45 120.22(15) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? C44 C45 C46 120.23(15) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C41 119.47(14) . . ? C45 C46 H46 120.3 . . ? C41 C46 H46 120.3 . . ? N1 C1 S1 178.43(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C10 C11 81.58(12) . . . . ? C31 P1 C10 C11 -162.01(10) . . . . ? C41 P1 C10 C11 -44.64(13) . . . . ? P1 C10 C11 C12 114.02(14) . . . . ? P1 C10 C11 C16 -68.07(18) . . . . ? C16 C11 C12 C13 -1.8(2) . . . . ? C10 C11 C12 C13 176.15(15) . . . . ? C11 C12 C13 C14 1.6(3) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C13 C14 C15 C16 -1.1(3) . . . . ? C12 C11 C16 C15 0.6(2) . . . . ? C10 C11 C16 C15 -177.26(15) . . . . ? C14 C15 C16 C11 0.8(3) . . . . ? C31 P1 C21 C22 65.11(13) . . . . ? C41 P1 C21 C22 -50.95(14) . . . . ? C10 P1 C21 C22 -176.28(11) . . . . ? C31 P1 C21 C26 -105.51(13) . . . . ? C41 P1 C21 C26 138.43(12) . . . . ? C10 P1 C21 C26 13.10(15) . . . . ? C26 C21 C22 C23 -0.3(2) . . . . ? P1 C21 C22 C23 -171.11(12) . . . . ? C21 C22 C23 C24 0.3(2) . . . . ? C22 C23 C24 C25 -0.9(2) . . . . ? C23 C24 C25 C26 1.6(2) . . . . ? C24 C25 C26 C21 -1.6(2) . . . . ? C22 C21 C26 C25 1.0(2) . . . . ? P1 C21 C26 C25 171.46(12) . . . . ? C21 P1 C31 C32 89.32(13) . . . . ? C41 P1 C31 C32 -150.87(12) . . . . ? C10 P1 C31 C32 -31.02(14) . . . . ? C21 P1 C31 C36 -84.05(13) . . . . ? C41 P1 C31 C36 35.76(14) . . . . ? C10 P1 C31 C36 155.61(12) . . . . ? C36 C31 C32 C33 0.7(2) . . . . ? P1 C31 C32 C33 -172.54(12) . . . . ? C31 C32 C33 C34 0.4(2) . . . . ? C32 C33 C34 C35 -1.5(2) . . . . ? C33 C34 C35 C36 1.4(3) . . . . ? C34 C35 C36 C31 -0.3(3) . . . . ? C32 C31 C36 C35 -0.8(2) . . . . ? P1 C31 C36 C35 172.59(13) . . . . ? C21 P1 C41 C46 -5.12(15) . . . . ? C31 P1 C41 C46 -120.40(13) . . . . ? C10 P1 C41 C46 120.77(13) . . . . ? C21 P1 C41 C42 170.54(11) . . . . ? C31 P1 C41 C42 55.26(13) . . . . ? C10 P1 C41 C42 -63.57(13) . . . . ? C46 C41 C42 C43 1.7(2) . . . . ? P1 C41 C42 C43 -174.11(12) . . . . ? C41 C42 C43 C44 0.3(2) . . . . ? C42 C43 C44 C45 -1.6(2) . . . . ? C43 C44 C45 C46 0.9(2) . . . . ? C44 C45 C46 C41 1.1(2) . . . . ? C42 C41 C46 C45 -2.4(2) . . . . ? P1 C41 C46 C45 173.10(12) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.583 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.078 # Attachment 'Complex_4.cif' data_110808f _database_code_depnum_ccdc_archive 'CCDC 760640' #TrackingRef 'Complex_4.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 P, F6 P' _chemical_formula_sum 'C25 H22 F6 P2' _chemical_formula_weight 498.37 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 61' _symmetry_space_group_name_Hall 'P 61' _symmetry_int_tables_number 169 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' _cell_length_a 9.9669(2) _cell_length_b 9.9669 _cell_length_c 40.3361(6) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 120.00 _cell_volume 3470.12(7) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 21605 _cell_measurement_theta_min 3.45 _cell_measurement_theta_max 28.76 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method ? _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96185 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60355 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -54 _diffrn_reflns_limit_l_max 54 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 28.80 _reflns_number_total 5801 _reflns_number_gt 4914 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0720P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(8) _refine_ls_number_reflns 5801 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1068 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.58478(6) 0.41589(6) 0.068853(13) 0.01572(12) Uani 1 1 d . . . C1 C 0.7717(3) 0.4943(3) 0.04868(5) 0.0193(5) Uani 1 1 d . . . H1A H 0.7686 0.5420 0.0274 0.023 Uiso 1 1 calc R . . H1B H 0.8514 0.5770 0.0628 0.023 Uiso 1 1 calc R . . C11 C 0.8181(3) 0.3746(3) 0.04212(6) 0.0195(5) Uani 1 1 d . . . C12 C 0.7615(3) 0.2771(3) 0.01473(6) 0.0248(5) Uani 1 1 d . . . H12 H 0.6940 0.2871 -0.0004 0.030 Uiso 1 1 calc R . . C13 C 0.8039(3) 0.1640(3) 0.00948(6) 0.0284(6) Uani 1 1 d . . . H13 H 0.7642 0.0970 -0.0091 0.034 Uiso 1 1 calc R . . C14 C 0.9031(3) 0.1498(3) 0.03128(7) 0.0301(6) Uani 1 1 d . . . H14 H 0.9322 0.0736 0.0276 0.036 Uiso 1 1 calc R . . C15 C 0.9603(3) 0.2475(3) 0.05871(7) 0.0303(6) Uani 1 1 d . . . H15 H 1.0286 0.2381 0.0737 0.036 Uiso 1 1 calc R . . C16 C 0.9177(3) 0.3582(3) 0.06411(6) 0.0250(5) Uani 1 1 d . . . H16 H 0.9565 0.4239 0.0830 0.030 Uiso 1 1 calc R . . C21 C 0.5883(3) 0.3304(3) 0.10781(6) 0.0193(5) Uani 1 1 d . . . C22 C 0.6100(3) 0.2019(3) 0.10857(6) 0.0236(5) Uani 1 1 d . . . H22 H 0.6135 0.1535 0.0886 0.028 Uiso 1 1 calc R . . C23 C 0.6263(3) 0.1463(3) 0.13903(7) 0.0347(6) Uani 1 1 d . . . H23 H 0.6427 0.0603 0.1398 0.042 Uiso 1 1 calc R . . C24 C 0.6189(4) 0.2148(4) 0.16809(7) 0.0438(8) Uani 1 1 d . . . H24 H 0.6298 0.1757 0.1888 0.053 Uiso 1 1 calc R . . C25 C 0.5955(4) 0.3406(4) 0.16721(7) 0.0414(7) Uani 1 1 d . . . H25 H 0.5897 0.3869 0.1874 0.050 Uiso 1 1 calc R . . C26 C 0.5807(3) 0.3995(3) 0.13721(6) 0.0308(6) Uani 1 1 d . . . H26 H 0.5654 0.4863 0.1367 0.037 Uiso 1 1 calc R . . C31 C 0.5399(3) 0.5664(3) 0.07620(5) 0.0191(5) Uani 1 1 d . . . C32 C 0.6479(3) 0.7221(3) 0.07321(6) 0.0242(5) Uani 1 1 d . . . H32 H 0.7509 0.7541 0.0665 0.029 Uiso 1 1 calc R . . C33 C 0.6037(3) 0.8321(3) 0.08021(7) 0.0300(6) Uani 1 1 d . . . H33 H 0.6773 0.9393 0.0782 0.036 Uiso 1 1 calc R . . C34 C 0.4543(3) 0.7860(3) 0.08995(6) 0.0234(5) Uani 1 1 d . . . H34 H 0.4255 0.8616 0.0947 0.028 Uiso 1 1 calc R . . C35 C 0.3460(3) 0.6301(3) 0.09293(7) 0.0275(5) Uani 1 1 d . . . H35 H 0.2432 0.5986 0.0998 0.033 Uiso 1 1 calc R . . C36 C 0.3884(3) 0.5198(3) 0.08582(7) 0.0273(5) Uani 1 1 d . . . H36 H 0.3142 0.4126 0.0875 0.033 Uiso 1 1 calc R . . C41 C 0.4376(3) 0.2804(3) 0.04135(5) 0.0180(4) Uani 1 1 d . . . C42 C 0.4216(3) 0.3396(3) 0.01147(6) 0.0269(5) Uani 1 1 d . . . H42 H 0.4857 0.4464 0.0065 0.032 Uiso 1 1 calc R . . C43 C 0.3105(3) 0.2409(4) -0.01119(7) 0.0333(6) Uani 1 1 d . . . H43 H 0.2979 0.2808 -0.0316 0.040 Uiso 1 1 calc R . . C44 C 0.2191(3) 0.0861(3) -0.00411(7) 0.0344(6) Uani 1 1 d . . . H44 H 0.1468 0.0186 -0.0201 0.041 Uiso 1 1 calc R . . C45 C 0.2316(3) 0.0279(3) 0.02607(7) 0.0341(6) Uani 1 1 d . . . H45 H 0.1651 -0.0785 0.0311 0.041 Uiso 1 1 calc R . . C46 C 0.3411(3) 0.1243(3) 0.04903(6) 0.0255(5) Uani 1 1 d . . . H46 H 0.3502 0.0845 0.0698 0.031 Uiso 1 1 calc R . . F1 F -0.1040(3) 0.6672(3) 0.12164(6) 0.0851(9) Uani 1 1 d . . . P2 P 0.06455(7) 0.81128(7) 0.123892(15) 0.02325(14) Uani 1 1 d . . . F2 F 0.1339(4) 0.7126(3) 0.13807(5) 0.0811(9) Uani 1 1 d . . . F3 F 0.2296(2) 0.9617(2) 0.12510(5) 0.0573(6) Uani 1 1 d . . . F4 F -0.0001(3) 0.9162(3) 0.10899(6) 0.0710(7) Uani 1 1 d . . . F5 F 0.09785(19) 0.77502(19) 0.08676(4) 0.0342(4) Uani 1 1 d . . . F6 F 0.0315(2) 0.8445(2) 0.16087(4) 0.0381(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0168(3) 0.0145(3) 0.0146(2) -0.0003(2) 0.0003(2) 0.0068(2) C1 0.0190(11) 0.0171(11) 0.0186(11) -0.0014(9) -0.0004(9) 0.0068(9) C11 0.0160(11) 0.0193(11) 0.0195(11) 0.0007(9) 0.0059(9) 0.0060(9) C12 0.0206(12) 0.0300(13) 0.0201(11) -0.0012(10) 0.0026(9) 0.0098(11) C13 0.0240(13) 0.0272(13) 0.0255(13) -0.0080(10) 0.0059(10) 0.0065(11) C14 0.0238(13) 0.0269(13) 0.0403(15) 0.0001(11) 0.0110(11) 0.0131(11) C15 0.0257(13) 0.0352(15) 0.0346(14) 0.0004(12) 0.0017(11) 0.0186(12) C16 0.0185(11) 0.0276(13) 0.0271(13) -0.0049(10) -0.0033(9) 0.0100(10) C21 0.0179(11) 0.0166(11) 0.0194(11) 0.0019(9) -0.0014(9) 0.0056(9) C22 0.0212(12) 0.0190(12) 0.0275(12) 0.0028(9) -0.0030(10) 0.0077(10) C23 0.0360(15) 0.0226(14) 0.0416(16) 0.0072(12) -0.0114(13) 0.0118(12) C24 0.0502(19) 0.0367(16) 0.0260(14) 0.0089(12) -0.0129(13) 0.0079(14) C25 0.056(2) 0.0360(16) 0.0201(13) 0.0012(12) -0.0030(13) 0.0138(15) C26 0.0421(16) 0.0277(14) 0.0178(11) -0.0022(10) -0.0004(11) 0.0138(12) C31 0.0220(11) 0.0199(11) 0.0158(11) 0.0001(8) -0.0020(9) 0.0108(9) C32 0.0216(12) 0.0216(12) 0.0300(13) 0.0033(10) 0.0031(10) 0.0112(10) C33 0.0328(14) 0.0178(12) 0.0364(15) 0.0026(10) 0.0031(11) 0.0103(11) C34 0.0298(13) 0.0238(12) 0.0233(11) -0.0013(10) -0.0015(10) 0.0184(11) C35 0.0223(12) 0.0261(13) 0.0365(14) -0.0079(11) -0.0003(10) 0.0138(11) C36 0.0218(12) 0.0169(11) 0.0367(14) -0.0037(10) 0.0034(10) 0.0047(10) C41 0.0163(10) 0.0188(11) 0.0169(10) -0.0045(8) 0.0002(8) 0.0072(9) C42 0.0242(13) 0.0277(13) 0.0212(12) -0.0002(10) -0.0007(10) 0.0073(11) C43 0.0259(14) 0.0475(17) 0.0193(12) -0.0003(11) -0.0034(10) 0.0129(13) C44 0.0240(13) 0.0391(16) 0.0277(13) -0.0083(12) -0.0018(11) 0.0064(12) C45 0.0266(14) 0.0247(14) 0.0364(15) -0.0031(11) -0.0007(11) 0.0018(11) C46 0.0237(12) 0.0215(12) 0.0273(13) 0.0018(10) -0.0014(10) 0.0081(10) F1 0.0565(14) 0.0673(15) 0.0602(14) -0.0287(12) 0.0188(11) -0.0225(11) P2 0.0231(3) 0.0235(3) 0.0217(3) -0.0037(2) -0.0005(2) 0.0106(3) F2 0.178(3) 0.111(2) 0.0300(9) 0.0016(11) 0.0023(12) 0.129(2) F3 0.0426(11) 0.0545(12) 0.0385(10) -0.0140(9) 0.0031(8) -0.0030(9) F4 0.0996(19) 0.1000(19) 0.0570(13) -0.0247(12) -0.0338(13) 0.0825(17) F5 0.0417(9) 0.0374(9) 0.0213(7) -0.0050(6) -0.0006(7) 0.0182(8) F6 0.0393(9) 0.0448(10) 0.0285(8) -0.0089(7) 0.0066(7) 0.0198(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C31 1.791(2) . ? P1 C41 1.796(2) . ? P1 C21 1.796(2) . ? P1 C1 1.814(2) . ? C1 C11 1.504(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C11 C12 1.391(4) . ? C11 C16 1.400(4) . ? C12 C13 1.404(4) . ? C12 H12 0.9500 . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 C15 1.394(4) . ? C14 H14 0.9500 . ? C15 C16 1.383(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.393(3) . ? C21 C22 1.402(3) . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 C24 1.377(4) . ? C23 H23 0.9500 . ? C24 C25 1.385(5) . ? C24 H24 0.9500 . ? C25 C26 1.385(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.383(3) . ? C31 C36 1.394(4) . ? C32 C33 1.399(4) . ? C32 H32 0.9500 . ? C33 C34 1.378(4) . ? C33 H33 0.9500 . ? C34 C35 1.385(4) . ? C34 H34 0.9500 . ? C35 C36 1.391(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.386(3) . ? C41 C46 1.394(3) . ? C42 C43 1.393(4) . ? C42 H42 0.9500 . ? C43 C44 1.373(4) . ? C43 H43 0.9500 . ? C44 C45 1.381(4) . ? C44 H44 0.9500 . ? C45 C46 1.387(4) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? F1 P2 1.575(2) . ? P2 F2 1.565(2) . ? P2 F3 1.5777(19) . ? P2 F4 1.596(2) . ? P2 F6 1.5975(16) . ? P2 F5 1.6136(16) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C41 106.27(11) . . ? C31 P1 C21 108.96(11) . . ? C41 P1 C21 112.70(11) . . ? C31 P1 C1 110.25(11) . . ? C41 P1 C1 108.89(11) . . ? C21 P1 C1 109.72(11) . . ? C11 C1 P1 113.22(16) . . ? C11 C1 H1A 108.9 . . ? P1 C1 H1A 108.9 . . ? C11 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C12 C11 C16 119.1(2) . . ? C12 C11 C1 121.0(2) . . ? C16 C11 C1 119.9(2) . . ? C11 C12 C13 120.0(2) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 119.8(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.7(2) . . ? C15 C16 H16 119.6 . . ? C11 C16 H16 119.6 . . ? C26 C21 C22 120.3(2) . . ? C26 C21 P1 119.44(19) . . ? C22 C21 P1 120.08(18) . . ? C23 C22 C21 119.1(2) . . ? C23 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.1(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 119.4(3) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? C32 C31 C36 120.2(2) . . ? C32 C31 P1 123.09(18) . . ? C36 C31 P1 116.69(18) . . ? C31 C32 C33 119.3(2) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C34 C33 C32 120.5(2) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 120.3(2) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 119.7(2) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C35 C36 C31 120.0(2) . . ? C35 C36 H36 120.0 . . ? C31 C36 H36 120.0 . . ? C42 C41 C46 120.4(2) . . ? C42 C41 P1 116.22(18) . . ? C46 C41 P1 123.39(18) . . ? C41 C42 C43 119.4(2) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C44 C43 C42 120.2(3) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C45 120.5(3) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C44 C45 C46 120.2(3) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C45 C46 C41 119.3(2) . . ? C45 C46 H46 120.3 . . ? C41 C46 H46 120.3 . . ? F2 P2 F1 93.05(18) . . ? F2 P2 F3 90.44(16) . . ? F1 P2 F3 176.51(17) . . ? F2 P2 F4 177.97(17) . . ? F1 P2 F4 88.82(16) . . ? F3 P2 F4 87.70(14) . . ? F2 P2 F6 89.45(10) . . ? F1 P2 F6 90.36(10) . . ? F3 P2 F6 89.96(10) . . ? F4 P2 F6 91.33(11) . . ? F2 P2 F5 89.63(10) . . ? F1 P2 F5 89.28(10) . . ? F3 P2 F5 90.46(9) . . ? F4 P2 F5 89.60(11) . . ? F6 P2 F5 178.99(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31 P1 C1 C11 179.24(16) . . . . ? C41 P1 C1 C11 -64.54(19) . . . . ? C21 P1 C1 C11 59.23(19) . . . . ? P1 C1 C11 C12 81.3(2) . . . . ? P1 C1 C11 C16 -97.6(2) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? C1 C11 C12 C13 -178.7(2) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? C12 C13 C14 C15 0.4(4) . . . . ? C13 C14 C15 C16 0.1(4) . . . . ? C14 C15 C16 C11 -0.5(4) . . . . ? C12 C11 C16 C15 0.4(4) . . . . ? C1 C11 C16 C15 179.3(2) . . . . ? C31 P1 C21 C26 -9.2(2) . . . . ? C41 P1 C21 C26 -126.9(2) . . . . ? C1 P1 C21 C26 111.6(2) . . . . ? C31 P1 C21 C22 175.44(18) . . . . ? C41 P1 C21 C22 57.7(2) . . . . ? C1 P1 C21 C22 -63.8(2) . . . . ? C26 C21 C22 C23 -1.1(4) . . . . ? P1 C21 C22 C23 174.3(2) . . . . ? C21 C22 C23 C24 1.0(4) . . . . ? C22 C23 C24 C25 -0.2(5) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C24 C25 C26 C21 0.5(5) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? P1 C21 C26 C25 -175.0(2) . . . . ? C41 P1 C31 C32 -130.5(2) . . . . ? C21 P1 C31 C32 107.8(2) . . . . ? C1 P1 C31 C32 -12.6(2) . . . . ? C41 P1 C31 C36 50.5(2) . . . . ? C21 P1 C31 C36 -71.2(2) . . . . ? C1 P1 C31 C36 168.37(18) . . . . ? C36 C31 C32 C33 0.5(4) . . . . ? P1 C31 C32 C33 -178.45(19) . . . . ? C31 C32 C33 C34 0.0(4) . . . . ? C32 C33 C34 C35 0.0(4) . . . . ? C33 C34 C35 C36 -0.4(4) . . . . ? C34 C35 C36 C31 0.9(4) . . . . ? C32 C31 C36 C35 -0.9(4) . . . . ? P1 C31 C36 C35 178.1(2) . . . . ? C31 P1 C41 C42 57.2(2) . . . . ? C21 P1 C41 C42 176.44(19) . . . . ? C1 P1 C41 C42 -61.6(2) . . . . ? C31 P1 C41 C46 -121.7(2) . . . . ? C21 P1 C41 C46 -2.4(2) . . . . ? C1 P1 C41 C46 119.6(2) . . . . ? C46 C41 C42 C43 -1.6(4) . . . . ? P1 C41 C42 C43 179.5(2) . . . . ? C41 C42 C43 C44 -0.7(4) . . . . ? C42 C43 C44 C45 2.8(4) . . . . ? C43 C44 C45 C46 -2.5(5) . . . . ? C44 C45 C46 C41 0.2(4) . . . . ? C42 C41 C46 C45 1.8(4) . . . . ? P1 C41 C46 C45 -179.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.710 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.056 # Attachment 'Complex_5a.cif' data_110808n _database_code_depnum_ccdc_archive 'CCDC 760641' #TrackingRef 'Complex_5a.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 P, C F3 O3 S' _chemical_formula_sum 'C26 H22 F3 O3 P S' _chemical_formula_weight 502.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.2246(4) _cell_length_b 19.4426(7) _cell_length_c 11.2114(4) _cell_angle_alpha 90.0 _cell_angle_beta 105.701(4) _cell_angle_gamma 90.0 _cell_volume 2355.43(15) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 11793 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 32.57 _exptl_crystal_description bar _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_method ? _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30215 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.67 _diffrn_reflns_theta_max 32.71 _reflns_number_total 8060 _reflns_number_gt 5850 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8060 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.16660(3) 0.132501(14) 0.15350(3) 0.01376(7) Uani 1 1 d . . . C10 C 0.04852(10) 0.06706(6) 0.10629(10) 0.0164(2) Uani 1 1 d . . . H10A H 0.0056 0.0738 0.0175 0.020 Uiso 1 1 calc R . . H10B H 0.0891 0.0214 0.1148 0.020 Uiso 1 1 calc R . . C11 C -0.04680(10) 0.06681(6) 0.17908(10) 0.0174(2) Uani 1 1 d . . . C12 C -0.15437(11) 0.10580(6) 0.14018(12) 0.0213(2) Uani 1 1 d . . . H12 H -0.1677 0.1333 0.0677 0.026 Uiso 1 1 calc R . . C13 C -0.24206(11) 0.10470(7) 0.20653(13) 0.0257(3) Uani 1 1 d . . . H13 H -0.3151 0.1316 0.1797 0.031 Uiso 1 1 calc R . . C14 C -0.22356(12) 0.06437(7) 0.31218(13) 0.0268(3) Uani 1 1 d . . . H14 H -0.2833 0.0639 0.3582 0.032 Uiso 1 1 calc R . . C15 C -0.11773(12) 0.02486(6) 0.34994(12) 0.0241(3) Uani 1 1 d . . . H15 H -0.1053 -0.0032 0.4216 0.029 Uiso 1 1 calc R . . C16 C -0.02970(11) 0.02576(6) 0.28440(11) 0.0203(2) Uani 1 1 d . . . H16 H 0.0427 -0.0017 0.3112 0.024 Uiso 1 1 calc R . . C21 C 0.25761(10) 0.11846(6) 0.30888(10) 0.0158(2) Uani 1 1 d . . . C22 C 0.20522(10) 0.12621(6) 0.40745(10) 0.0179(2) Uani 1 1 d . . . H22 H 0.1220 0.1412 0.3929 0.021 Uiso 1 1 calc R . . C23 C 0.27547(11) 0.11189(6) 0.52701(11) 0.0213(2) Uani 1 1 d . . . H23 H 0.2403 0.1172 0.5946 0.026 Uiso 1 1 calc R . . C24 C 0.39668(12) 0.08988(7) 0.54815(11) 0.0239(3) Uani 1 1 d . . . H24 H 0.4440 0.0796 0.6301 0.029 Uiso 1 1 calc R . . C25 C 0.44911(11) 0.08285(7) 0.45066(11) 0.0253(3) Uani 1 1 d . . . H25 H 0.5328 0.0684 0.4658 0.030 Uiso 1 1 calc R . . C26 C 0.37994(10) 0.09677(6) 0.33102(11) 0.0205(2) Uani 1 1 d . . . H26 H 0.4158 0.0915 0.2639 0.025 Uiso 1 1 calc R . . C31 C 0.26701(10) 0.12933(6) 0.05392(10) 0.0168(2) Uani 1 1 d . . . C32 C 0.28844(12) 0.06795(6) -0.00091(11) 0.0224(2) Uani 1 1 d . . . H32 H 0.2450 0.0273 0.0088 0.027 Uiso 1 1 calc R . . C33 C 0.37413(13) 0.06695(8) -0.07003(12) 0.0303(3) Uani 1 1 d . . . H33 H 0.3890 0.0254 -0.1083 0.036 Uiso 1 1 calc R . . C34 C 0.43773(12) 0.12566(8) -0.08357(12) 0.0301(3) Uani 1 1 d . . . H34 H 0.4966 0.1243 -0.1305 0.036 Uiso 1 1 calc R . . C35 C 0.41647(11) 0.18685(7) -0.02912(12) 0.0269(3) Uani 1 1 d . . . H35 H 0.4603 0.2273 -0.0392 0.032 Uiso 1 1 calc R . . C36 C 0.33120(11) 0.18880(6) 0.03991(11) 0.0207(2) Uani 1 1 d . . . H36 H 0.3165 0.2306 0.0776 0.025 Uiso 1 1 calc R . . C41 C 0.09532(10) 0.21520(5) 0.13676(10) 0.0144(2) Uani 1 1 d . . . C42 C 0.01044(10) 0.23059(6) 0.02319(10) 0.0169(2) Uani 1 1 d . . . H42 H -0.0094 0.1970 -0.0408 0.020 Uiso 1 1 calc R . . C43 C -0.04427(10) 0.29470(6) 0.00454(11) 0.0195(2) Uani 1 1 d . . . H43 H -0.1017 0.3053 -0.0725 0.023 Uiso 1 1 calc R . . C44 C -0.01549(11) 0.34372(6) 0.09813(11) 0.0206(2) Uani 1 1 d . . . H44 H -0.0541 0.3876 0.0854 0.025 Uiso 1 1 calc R . . C45 C 0.06934(11) 0.32873(6) 0.20994(11) 0.0214(2) Uani 1 1 d . . . H45 H 0.0894 0.3626 0.2733 0.026 Uiso 1 1 calc R . . C46 C 0.12498(10) 0.26478(6) 0.22981(11) 0.0178(2) Uani 1 1 d . . . H46 H 0.1832 0.2547 0.3066 0.021 Uiso 1 1 calc R . . S1 S 0.74325(3) 0.095959(14) 0.75051(3) 0.01710(7) Uani 1 1 d . . . O1 O 0.86613(8) 0.09524(4) 0.83426(8) 0.02244(18) Uani 1 1 d . . . O2 O 0.65058(8) 0.06321(4) 0.79777(8) 0.0257(2) Uani 1 1 d . . . O3 O 0.73784(8) 0.08056(5) 0.62400(8) 0.02442(19) Uani 1 1 d . . . C1 C 0.70265(12) 0.18703(7) 0.74835(12) 0.0249(3) Uani 1 1 d . . . F1 F 0.59067(8) 0.19917(4) 0.67334(9) 0.0448(2) Uani 1 1 d . . . F2 F 0.78314(8) 0.22620(4) 0.71275(9) 0.0400(2) Uani 1 1 d . . . F3 F 0.70055(7) 0.20832(4) 0.86121(8) 0.0356(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01486(13) 0.01284(13) 0.01272(13) -0.00066(10) 0.00228(10) 0.00077(11) C10 0.0192(5) 0.0121(5) 0.0158(5) 0.0001(4) 0.0012(4) -0.0003(4) C11 0.0184(5) 0.0137(5) 0.0182(5) -0.0014(4) 0.0018(4) -0.0044(4) C12 0.0195(5) 0.0186(5) 0.0237(6) 0.0033(5) 0.0020(5) -0.0025(5) C13 0.0196(6) 0.0228(6) 0.0345(7) -0.0003(5) 0.0072(5) -0.0008(5) C14 0.0246(6) 0.0260(7) 0.0319(7) -0.0039(5) 0.0112(5) -0.0079(5) C15 0.0279(6) 0.0217(6) 0.0216(6) 0.0025(5) 0.0051(5) -0.0066(5) C16 0.0215(5) 0.0162(5) 0.0209(6) 0.0016(4) 0.0018(5) -0.0025(5) C21 0.0161(5) 0.0152(5) 0.0150(5) 0.0000(4) 0.0022(4) -0.0010(4) C22 0.0176(5) 0.0183(5) 0.0175(5) -0.0019(4) 0.0044(4) -0.0018(4) C23 0.0247(6) 0.0236(6) 0.0155(5) -0.0010(4) 0.0051(5) -0.0037(5) C24 0.0249(6) 0.0276(6) 0.0148(5) 0.0023(5) -0.0020(5) -0.0017(5) C25 0.0174(5) 0.0333(7) 0.0220(6) 0.0017(5) 0.0000(5) 0.0036(5) C26 0.0172(5) 0.0260(6) 0.0176(6) -0.0006(5) 0.0032(4) 0.0020(5) C31 0.0171(5) 0.0188(5) 0.0130(5) 0.0000(4) 0.0018(4) 0.0032(4) C32 0.0259(6) 0.0203(6) 0.0211(6) -0.0040(5) 0.0064(5) 0.0031(5) C33 0.0315(7) 0.0354(8) 0.0257(7) -0.0093(6) 0.0108(6) 0.0076(6) C34 0.0241(6) 0.0459(8) 0.0233(6) -0.0044(6) 0.0113(5) 0.0036(6) C35 0.0233(6) 0.0341(7) 0.0251(7) 0.0007(5) 0.0095(5) -0.0032(5) C36 0.0219(5) 0.0208(6) 0.0199(6) -0.0008(5) 0.0067(5) 0.0014(5) C41 0.0146(5) 0.0128(5) 0.0164(5) -0.0008(4) 0.0053(4) -0.0004(4) C42 0.0175(5) 0.0154(5) 0.0172(5) -0.0014(4) 0.0035(4) -0.0012(4) C43 0.0175(5) 0.0176(5) 0.0225(6) 0.0025(4) 0.0039(4) 0.0006(4) C44 0.0221(5) 0.0137(5) 0.0284(6) 0.0004(5) 0.0108(5) 0.0030(5) C45 0.0268(6) 0.0167(5) 0.0224(6) -0.0055(4) 0.0097(5) -0.0018(5) C46 0.0203(5) 0.0167(5) 0.0165(5) -0.0021(4) 0.0051(4) -0.0006(4) S1 0.01657(13) 0.01610(13) 0.01754(14) 0.00097(10) 0.00273(10) 0.00165(11) O1 0.0196(4) 0.0244(5) 0.0197(4) -0.0010(3) -0.0010(3) 0.0049(4) O2 0.0269(4) 0.0228(4) 0.0310(5) 0.0023(4) 0.0139(4) -0.0014(4) O3 0.0248(4) 0.0297(5) 0.0175(4) -0.0018(3) 0.0034(3) -0.0016(4) C1 0.0221(6) 0.0192(6) 0.0308(7) 0.0019(5) 0.0027(5) 0.0024(5) F1 0.0330(4) 0.0284(4) 0.0579(6) 0.0036(4) -0.0135(4) 0.0125(4) F2 0.0467(5) 0.0194(4) 0.0585(6) 0.0062(4) 0.0220(4) -0.0032(4) F3 0.0377(4) 0.0265(4) 0.0437(5) -0.0108(4) 0.0129(4) 0.0051(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C41 1.7830(11) . ? P1 C21 1.7860(11) . ? P1 C31 1.7893(11) . ? P1 C10 1.8100(11) . ? C10 C11 1.5111(16) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.3920(16) . ? C11 C16 1.3948(16) . ? C12 C13 1.3853(17) . ? C12 H12 0.9500 . ? C13 C14 1.3885(19) . ? C13 H13 0.9500 . ? C14 C15 1.3813(19) . ? C14 H14 0.9500 . ? C15 C16 1.3818(17) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.3930(15) . ? C21 C22 1.3934(15) . ? C22 C23 1.3870(16) . ? C22 H22 0.9500 . ? C23 C24 1.3841(17) . ? C23 H23 0.9500 . ? C24 C25 1.3813(17) . ? C24 H24 0.9500 . ? C25 C26 1.3825(16) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.3928(16) . ? C31 C36 1.3936(16) . ? C32 C33 1.3891(17) . ? C32 H32 0.9500 . ? C33 C34 1.376(2) . ? C33 H33 0.9500 . ? C34 C35 1.387(2) . ? C34 H34 0.9500 . ? C35 C36 1.3847(16) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C46 1.3929(15) . ? C41 C42 1.4008(15) . ? C42 C43 1.3801(16) . ? C42 H42 0.9500 . ? C43 C44 1.3894(17) . ? C43 H43 0.9500 . ? C44 C45 1.3846(17) . ? C44 H44 0.9500 . ? C45 C46 1.3823(16) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? S1 O3 1.4347(9) . ? S1 O2 1.4376(9) . ? S1 O1 1.4433(9) . ? S1 C1 1.8268(13) . ? C1 F2 1.3232(15) . ? C1 F1 1.3307(14) . ? C1 F3 1.3376(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C41 P1 C21 111.25(5) . . ? C41 P1 C31 107.81(5) . . ? C21 P1 C31 108.22(5) . . ? C41 P1 C10 109.33(5) . . ? C21 P1 C10 110.98(5) . . ? C31 P1 C10 109.17(5) . . ? C11 C10 P1 114.44(8) . . ? C11 C10 H10A 108.6 . . ? P1 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? P1 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C12 C11 C16 119.07(11) . . ? C12 C11 C10 120.66(10) . . ? C16 C11 C10 120.25(10) . . ? C13 C12 C11 120.36(11) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C14 120.19(12) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.55(12) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.63(12) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 120.20(11) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C26 C21 C22 119.91(10) . . ? C26 C21 P1 119.74(9) . . ? C22 C21 P1 120.29(8) . . ? C23 C22 C21 119.55(10) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C24 C23 C22 120.19(11) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 120.31(11) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.04(11) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.99(11) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C32 C31 C36 120.32(11) . . ? C32 C31 P1 121.20(9) . . ? C36 C31 P1 118.29(8) . . ? C33 C32 C31 119.12(12) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C34 C33 C32 120.53(12) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 120.44(12) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C36 C35 C34 119.79(13) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C35 C36 C31 119.79(11) . . ? C35 C36 H36 120.1 . . ? C31 C36 H36 120.1 . . ? C46 C41 C42 119.92(10) . . ? C46 C41 P1 122.39(9) . . ? C42 C41 P1 117.63(8) . . ? C43 C42 C41 119.73(10) . . ? C43 C42 H42 120.1 . . ? C41 C42 H42 120.1 . . ? C42 C43 C44 120.14(11) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C45 C44 C43 120.11(11) . . ? C45 C44 H44 119.9 . . ? C43 C44 H44 119.9 . . ? C46 C45 C44 120.35(11) . . ? C46 C45 H45 119.8 . . ? C44 C45 H45 119.8 . . ? C45 C46 C41 119.73(11) . . ? C45 C46 H46 120.1 . . ? C41 C46 H46 120.1 . . ? O3 S1 O2 115.51(5) . . ? O3 S1 O1 114.73(5) . . ? O2 S1 O1 114.54(5) . . ? O3 S1 C1 104.21(6) . . ? O2 S1 C1 103.38(6) . . ? O1 S1 C1 102.07(5) . . ? F2 C1 F1 108.21(11) . . ? F2 C1 F3 107.18(10) . . ? F1 C1 F3 106.71(10) . . ? F2 C1 S1 111.94(9) . . ? F1 C1 S1 111.72(9) . . ? F3 C1 S1 110.83(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C41 P1 C10 C11 -59.17(9) . . . . ? C21 P1 C10 C11 63.91(9) . . . . ? C31 P1 C10 C11 -176.88(8) . . . . ? P1 C10 C11 C12 90.16(12) . . . . ? P1 C10 C11 C16 -91.76(11) . . . . ? C16 C11 C12 C13 1.13(18) . . . . ? C10 C11 C12 C13 179.23(11) . . . . ? C11 C12 C13 C14 -0.32(19) . . . . ? C12 C13 C14 C15 -0.6(2) . . . . ? C13 C14 C15 C16 0.74(19) . . . . ? C14 C15 C16 C11 0.09(19) . . . . ? C12 C11 C16 C15 -1.02(17) . . . . ? C10 C11 C16 C15 -179.13(10) . . . . ? C41 P1 C21 C26 -128.57(9) . . . . ? C31 P1 C21 C26 -10.30(11) . . . . ? C10 P1 C21 C26 109.47(10) . . . . ? C41 P1 C21 C22 54.23(11) . . . . ? C31 P1 C21 C22 172.49(9) . . . . ? C10 P1 C21 C22 -67.74(10) . . . . ? C26 C21 C22 C23 -0.30(17) . . . . ? P1 C21 C22 C23 176.89(9) . . . . ? C21 C22 C23 C24 -0.16(18) . . . . ? C22 C23 C24 C25 0.82(19) . . . . ? C23 C24 C25 C26 -1.0(2) . . . . ? C24 C25 C26 C21 0.54(19) . . . . ? C22 C21 C26 C25 0.12(18) . . . . ? P1 C21 C26 C25 -177.10(10) . . . . ? C41 P1 C31 C32 -148.44(10) . . . . ? C21 P1 C31 C32 91.13(10) . . . . ? C10 P1 C31 C32 -29.78(11) . . . . ? C41 P1 C31 C36 36.49(10) . . . . ? C21 P1 C31 C36 -83.95(10) . . . . ? C10 P1 C31 C36 155.15(9) . . . . ? C36 C31 C32 C33 -0.28(18) . . . . ? P1 C31 C32 C33 -175.25(10) . . . . ? C31 C32 C33 C34 0.4(2) . . . . ? C32 C33 C34 C35 -0.5(2) . . . . ? C33 C34 C35 C36 0.4(2) . . . . ? C34 C35 C36 C31 -0.20(19) . . . . ? C32 C31 C36 C35 0.16(17) . . . . ? P1 C31 C36 C35 175.28(9) . . . . ? C21 P1 C41 C46 9.34(11) . . . . ? C31 P1 C41 C46 -109.17(9) . . . . ? C10 P1 C41 C46 132.26(9) . . . . ? C21 P1 C41 C42 -173.30(8) . . . . ? C31 P1 C41 C42 68.19(9) . . . . ? C10 P1 C41 C42 -50.38(10) . . . . ? C46 C41 C42 C43 -0.61(16) . . . . ? P1 C41 C42 C43 -178.04(8) . . . . ? C41 C42 C43 C44 -0.14(16) . . . . ? C42 C43 C44 C45 0.79(17) . . . . ? C43 C44 C45 C46 -0.69(17) . . . . ? C44 C45 C46 C41 -0.07(17) . . . . ? C42 C41 C46 C45 0.71(16) . . . . ? P1 C41 C46 C45 178.01(9) . . . . ? O3 S1 C1 F2 -62.15(10) . . . . ? O2 S1 C1 F2 176.73(9) . . . . ? O1 S1 C1 F2 57.55(10) . . . . ? O3 S1 C1 F1 59.39(10) . . . . ? O2 S1 C1 F1 -61.73(11) . . . . ? O1 S1 C1 F1 179.09(9) . . . . ? O3 S1 C1 F3 178.25(8) . . . . ? O2 S1 C1 F3 57.12(10) . . . . ? O1 S1 C1 F3 -62.05(9) . . . . ? _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.404 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.058 # Attachment 'Complex_5b.cif' data_110808n_2 _database_code_depnum_ccdc_archive 'CCDC 760642' #TrackingRef 'Complex_5b.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 P, C F3 O3 S' _chemical_formula_sum 'C26 H22 F3 O3 P S' _chemical_formula_weight 502.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7892(4) _cell_length_b 11.4559(6) _cell_length_c 21.464(1) _cell_angle_alpha 88.629(4) _cell_angle_beta 86.009(3) _cell_angle_gamma 75.805(4) _cell_volume 2327.85(19) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3982 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method ? _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.259 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15366 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.1295 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 8178 _reflns_number_gt 4573 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00199(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8178 _refine_ls_number_parameters 614 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0974 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.0685 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 0.800 _refine_ls_restrained_S_all 0.800 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.53033(7) 0.84835(6) 0.14454(3) 0.01708(18) Uani 1 1 d . . . C10 C 0.4443(2) 0.8865(2) 0.07250(11) 0.0177(7) Uani 1 1 d . . . H10A H 0.4037 0.9746 0.0715 0.021 Uiso 1 1 calc R . . H10B H 0.5167 0.8668 0.0373 0.021 Uiso 1 1 calc R . . C111 C 0.3271(3) 0.8237(2) 0.06189(11) 0.0166(6) Uani 1 1 d . . . C112 C 0.1877(3) 0.8895(2) 0.06158(11) 0.0201(7) Uani 1 1 d . . . H112 H 0.1640 0.9728 0.0713 0.024 Uiso 1 1 calc R . . C113 C 0.0823(3) 0.8337(3) 0.04707(12) 0.0226(7) Uani 1 1 d . . . H113 H -0.0127 0.8794 0.0462 0.027 Uiso 1 1 calc R . . C114 C 0.1159(3) 0.7120(3) 0.03401(12) 0.0245(7) Uani 1 1 d . . . H114 H 0.0441 0.6740 0.0242 0.029 Uiso 1 1 calc R . . C115 C 0.2540(3) 0.6460(3) 0.03517(11) 0.0223(7) Uani 1 1 d . . . H115 H 0.2771 0.5621 0.0267 0.027 Uiso 1 1 calc R . . C116 C 0.3591(3) 0.7016(2) 0.04870(11) 0.0197(7) Uani 1 1 d . . . H116 H 0.4541 0.6556 0.0490 0.024 Uiso 1 1 calc R . . C121 C 0.6653(2) 0.9301(2) 0.14827(12) 0.0162(6) Uani 1 1 d . . . C122 C 0.6878(3) 1.0113(2) 0.10189(12) 0.0217(7) Uani 1 1 d . . . H122 H 0.6366 1.0203 0.0653 0.026 Uiso 1 1 calc R . . C123 C 0.7849(3) 1.0790(2) 0.10907(13) 0.0254(7) Uani 1 1 d . . . H123 H 0.7994 1.1350 0.0775 0.031 Uiso 1 1 calc R . . C124 C 0.8612(3) 1.0659(2) 0.16177(13) 0.0231(7) Uani 1 1 d . . . H124 H 0.9274 1.1128 0.1666 0.028 Uiso 1 1 calc R . . C125 C 0.8398(3) 0.9835(2) 0.20742(13) 0.0239(7) Uani 1 1 d . . . H125 H 0.8922 0.9737 0.2436 0.029 Uiso 1 1 calc R . . C126 C 0.7434(2) 0.9155(2) 0.20092(12) 0.0203(7) Uani 1 1 d . . . H126 H 0.7303 0.8588 0.2324 0.024 Uiso 1 1 calc R . . C131 C 0.4097(3) 0.8902(2) 0.21173(12) 0.0158(6) Uani 1 1 d . . . C132 C 0.2923(3) 0.9862(2) 0.20711(13) 0.0195(7) Uani 1 1 d . . . H132 H 0.2707 1.0232 0.1677 0.023 Uiso 1 1 calc R . . C133 C 0.2068(3) 1.0280(3) 0.26009(13) 0.0247(7) Uani 1 1 d . . . H133 H 0.1269 1.0940 0.2571 0.030 Uiso 1 1 calc R . . C134 C 0.2377(3) 0.9734(3) 0.31744(13) 0.0268(7) Uani 1 1 d . . . H134 H 0.1784 1.0019 0.3536 0.032 Uiso 1 1 calc R . . C135 C 0.3540(3) 0.8782(3) 0.32242(13) 0.0263(7) Uani 1 1 d . . . H135 H 0.3747 0.8415 0.3619 0.032 Uiso 1 1 calc R . . C136 C 0.4406(3) 0.8360(2) 0.27006(12) 0.0214(7) Uani 1 1 d . . . H136 H 0.5209 0.7705 0.2735 0.026 Uiso 1 1 calc R . . C141 C 0.6114(3) 0.6895(2) 0.14408(12) 0.0164(6) Uani 1 1 d . . . C142 C 0.5411(3) 0.6072(2) 0.17196(12) 0.0226(7) Uani 1 1 d . . . H142 H 0.4540 0.6342 0.1958 0.027 Uiso 1 1 calc R . . C143 C 0.6014(3) 0.4853(3) 0.16394(13) 0.0259(7) Uani 1 1 d . . . H143 H 0.5559 0.4281 0.1832 0.031 Uiso 1 1 calc R . . C144 C 0.7270(3) 0.4460(3) 0.12831(13) 0.0280(7) Uani 1 1 d . . . H144 H 0.7671 0.3622 0.1233 0.034 Uiso 1 1 calc R . . C145 C 0.7941(3) 0.5281(3) 0.09999(13) 0.0257(7) Uani 1 1 d . . . H145 H 0.8793 0.5007 0.0748 0.031 Uiso 1 1 calc R . . C146 C 0.7371(3) 0.6511(3) 0.10829(12) 0.0210(7) Uani 1 1 d . . . H146 H 0.7838 0.7079 0.0896 0.025 Uiso 1 1 calc R . . P2 P 0.20694(7) 0.45367(6) 0.37272(3) 0.01514(18) Uani 1 1 d . . . C20 C 0.0498(2) 0.4347(2) 0.41722(11) 0.0166(6) Uani 1 1 d . . . H20A H 0.0774 0.3767 0.4517 0.020 Uiso 1 1 calc R . . H20B H -0.0015 0.5128 0.4358 0.020 Uiso 1 1 calc R . . C211 C -0.0473(2) 0.3896(2) 0.37696(12) 0.0172(7) Uani 1 1 d . . . C212 C -0.0349(3) 0.2676(2) 0.36917(12) 0.0224(7) Uani 1 1 d . . . H212 H 0.0328 0.2102 0.3909 0.027 Uiso 1 1 calc R . . C213 C -0.1213(3) 0.2294(3) 0.32965(13) 0.0304(8) Uani 1 1 d . . . H213 H -0.1131 0.1458 0.3246 0.036 Uiso 1 1 calc R . . C214 C -0.2187(3) 0.3121(3) 0.29774(13) 0.0315(8) Uani 1 1 d . . . H214 H -0.2753 0.2855 0.2696 0.038 Uiso 1 1 calc R . . C215 C -0.2342(3) 0.4338(3) 0.30665(13) 0.0295(8) Uani 1 1 d . . . H215 H -0.3037 0.4909 0.2857 0.035 Uiso 1 1 calc R . . C216 C -0.1485(2) 0.4726(2) 0.34605(12) 0.0212(7) Uani 1 1 d . . . H216 H -0.1590 0.5564 0.3519 0.025 Uiso 1 1 calc R . . C221 C 0.2945(2) 0.5392(2) 0.41775(12) 0.0155(6) Uani 1 1 d . . . C222 C 0.2183(3) 0.6264(2) 0.45889(12) 0.0226(7) Uani 1 1 d . . . H222 H 0.1194 0.6358 0.4666 0.027 Uiso 1 1 calc R . . C223 C 0.2862(3) 0.7002(2) 0.48903(12) 0.0248(7) Uani 1 1 d . . . H223 H 0.2340 0.7591 0.5177 0.030 Uiso 1 1 calc R . . C224 C 0.4299(3) 0.6876(3) 0.47726(12) 0.0235(7) Uani 1 1 d . . . H224 H 0.4761 0.7392 0.4970 0.028 Uiso 1 1 calc R . . C225 C 0.5056(3) 0.6002(2) 0.43687(13) 0.0220(7) Uani 1 1 d . . . H225 H 0.6044 0.5913 0.4294 0.026 Uiso 1 1 calc R . . C226 C 0.4405(3) 0.5249(2) 0.40693(12) 0.0199(7) Uani 1 1 d . . . H226 H 0.4940 0.4643 0.3794 0.024 Uiso 1 1 calc R . . C231 C 0.3237(2) 0.3095(2) 0.35593(12) 0.0140(6) Uani 1 1 d . . . C232 C 0.3558(2) 0.2288(2) 0.40567(12) 0.0173(6) Uani 1 1 d . . . H232 H 0.3090 0.2477 0.4458 0.021 Uiso 1 1 calc R . . C233 C 0.4563(3) 0.1212(2) 0.39629(13) 0.0216(7) Uani 1 1 d . . . H233 H 0.4784 0.0661 0.4300 0.026 Uiso 1 1 calc R . . C234 C 0.5245(2) 0.0937(2) 0.33795(13) 0.0203(7) Uani 1 1 d . . . H234 H 0.5940 0.0202 0.3319 0.024 Uiso 1 1 calc R . . C235 C 0.4920(2) 0.1728(2) 0.28839(12) 0.0194(7) Uani 1 1 d . . . H235 H 0.5375 0.1528 0.2482 0.023 Uiso 1 1 calc R . . C236 C 0.3928(2) 0.2814(2) 0.29766(13) 0.0181(7) Uani 1 1 d . . . H236 H 0.3721 0.3368 0.2639 0.022 Uiso 1 1 calc R . . C241 C 0.1589(2) 0.5346(2) 0.30199(12) 0.0157(6) Uani 1 1 d . . . C242 C 0.1072(2) 0.4806(2) 0.25413(12) 0.0200(7) Uani 1 1 d . . . H242 H 0.1028 0.3988 0.2577 0.024 Uiso 1 1 calc R . . C243 C 0.0626(3) 0.5470(3) 0.20166(13) 0.0280(7) Uani 1 1 d . . . H243 H 0.0285 0.5105 0.1687 0.034 Uiso 1 1 calc R . . C244 C 0.0674(3) 0.6671(3) 0.19681(14) 0.0312(8) Uani 1 1 d . . . H244 H 0.0349 0.7128 0.1609 0.037 Uiso 1 1 calc R . . C245 C 0.1191(3) 0.7199(3) 0.24376(13) 0.0280(7) Uani 1 1 d . . . H245 H 0.1238 0.8017 0.2398 0.034 Uiso 1 1 calc R . . C246 C 0.1641(2) 0.6548(2) 0.29657(13) 0.0217(7) Uani 1 1 d . . . H246 H 0.1987 0.6919 0.3292 0.026 Uiso 1 1 calc R . . S1 S 0.19760(7) 0.26205(7) 0.07256(3) 0.02293(19) Uani 1 1 d . . . O11 O 0.26247(18) 0.16554(17) 0.02932(9) 0.0322(5) Uani 1 1 d . . . O12 O 0.11817(18) 0.22688(18) 0.12553(9) 0.0376(6) Uani 1 1 d . . . O13 O 0.13401(17) 0.37524(16) 0.04394(8) 0.0277(5) Uani 1 1 d . . . C1 C 0.3501(3) 0.2920(3) 0.10678(13) 0.0244(7) Uani 1 1 d . . . F11 F 0.31655(16) 0.38584(16) 0.14510(8) 0.0393(5) Uani 1 1 d . . . F12 F 0.44342(15) 0.31556(15) 0.06307(7) 0.0384(5) Uani 1 1 d . . . F13 F 0.41812(16) 0.19775(15) 0.13974(8) 0.0447(5) Uani 1 1 d . . . S2 S -0.22298(7) 0.81257(6) 0.41883(3) 0.02071(18) Uani 1 1 d . . . O21 O -0.15170(17) 0.70071(15) 0.44795(8) 0.0248(5) Uani 1 1 d . . . O22 O -0.36284(17) 0.86365(16) 0.44535(9) 0.0278(5) Uani 1 1 d . . . O23 O -0.2061(2) 0.81480(18) 0.35172(9) 0.0390(5) Uani 1 1 d . . . C2 C -0.1237(3) 0.9161(3) 0.44294(15) 0.0344(8) Uani 1 1 d . . . F21 F -0.17900(18) 1.02839(15) 0.42410(8) 0.0504(5) Uani 1 1 d . . . F22 F 0.00987(17) 0.88649(17) 0.41996(10) 0.0662(7) Uani 1 1 d . . . F23 F -0.1214(2) 0.91863(16) 0.50488(8) 0.0580(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0177(4) 0.0168(4) 0.0170(4) 0.0002(4) -0.0015(3) -0.0049(3) C10 0.0196(14) 0.0164(16) 0.0177(16) 0.0016(13) -0.0013(12) -0.0058(13) C111 0.0197(15) 0.0217(18) 0.0092(15) 0.0033(13) -0.0032(12) -0.0062(14) C112 0.0219(15) 0.0214(17) 0.0176(16) -0.0027(13) 0.0008(13) -0.0065(14) C113 0.0180(15) 0.0315(19) 0.0177(17) 0.0005(15) -0.0047(13) -0.0041(14) C114 0.0287(17) 0.034(2) 0.0156(17) 0.0023(15) -0.0039(14) -0.0169(16) C115 0.0337(17) 0.0225(18) 0.0138(16) -0.0004(14) -0.0046(14) -0.0119(15) C116 0.0195(15) 0.0246(18) 0.0137(16) 0.0019(14) -0.0034(12) -0.0025(14) C121 0.0162(14) 0.0127(15) 0.0180(16) -0.0014(13) 0.0011(13) -0.0008(12) C122 0.0221(15) 0.0245(17) 0.0188(17) 0.0005(14) -0.0034(13) -0.0058(14) C123 0.0298(16) 0.0237(18) 0.0237(18) -0.0004(15) 0.0041(14) -0.0096(15) C124 0.0179(15) 0.0222(17) 0.0316(19) -0.0114(15) 0.0053(14) -0.0101(14) C125 0.0172(15) 0.0261(18) 0.0283(18) -0.0056(15) -0.0056(13) -0.0037(14) C126 0.0205(15) 0.0147(16) 0.0247(17) -0.0014(14) -0.0014(13) -0.0022(13) C131 0.0181(14) 0.0157(16) 0.0161(16) -0.0040(13) 0.0004(12) -0.0091(14) C132 0.0204(15) 0.0213(17) 0.0186(17) 0.0014(14) -0.0014(13) -0.0085(14) C133 0.0185(15) 0.0245(18) 0.032(2) -0.0055(16) 0.0012(14) -0.0076(14) C134 0.0298(17) 0.032(2) 0.0211(18) -0.0105(16) 0.0093(14) -0.0152(16) C135 0.0397(18) 0.0286(19) 0.0158(17) 0.0011(15) -0.0001(15) -0.0193(17) C136 0.0254(16) 0.0176(17) 0.0236(18) 0.0008(14) -0.0017(14) -0.0099(14) C141 0.0196(15) 0.0155(16) 0.0158(16) 0.0009(13) -0.0068(13) -0.0058(13) C142 0.0242(15) 0.0253(19) 0.0206(17) 0.0038(15) -0.0100(13) -0.0084(15) C143 0.0390(18) 0.0210(19) 0.0224(18) 0.0038(15) -0.0101(15) -0.0144(16) C144 0.0404(18) 0.0138(17) 0.0292(19) -0.0040(15) -0.0134(16) -0.0020(16) C145 0.0276(16) 0.0248(19) 0.0227(18) -0.0058(15) -0.0093(14) 0.0001(15) C146 0.0237(16) 0.0214(18) 0.0194(17) 0.0017(14) -0.0073(13) -0.0070(14) P2 0.0155(4) 0.0145(4) 0.0147(4) -0.0002(3) -0.0020(3) -0.0021(3) C20 0.0188(14) 0.0168(16) 0.0135(15) 0.0005(13) -0.0003(12) -0.0033(13) C211 0.0170(14) 0.0211(17) 0.0148(16) -0.0008(14) 0.0039(12) -0.0086(14) C212 0.0234(16) 0.0244(18) 0.0193(17) 0.0000(14) 0.0053(13) -0.0076(14) C213 0.0344(18) 0.0284(19) 0.0325(19) -0.0088(16) 0.0086(16) -0.0180(17) C214 0.0272(17) 0.046(2) 0.0270(19) -0.0141(17) 0.0029(15) -0.0201(17) C215 0.0176(15) 0.042(2) 0.0282(19) -0.0045(16) -0.0050(14) -0.0035(15) C216 0.0171(14) 0.0225(17) 0.0237(17) -0.0072(14) -0.0041(13) -0.0031(14) C221 0.0152(14) 0.0157(16) 0.0154(16) 0.0017(13) -0.0037(12) -0.0027(13) C222 0.0193(15) 0.0240(18) 0.0257(18) -0.0026(15) -0.0009(13) -0.0078(14) C223 0.0306(17) 0.0256(18) 0.0200(17) -0.0123(14) 0.0019(13) -0.0099(15) C224 0.0300(17) 0.0257(19) 0.0199(17) 0.0016(15) -0.0075(14) -0.0150(16) C225 0.0151(14) 0.0239(18) 0.0281(18) 0.0008(15) -0.0054(14) -0.0058(14) C226 0.0185(15) 0.0186(17) 0.0208(17) -0.0008(14) -0.0017(13) -0.0006(13) C231 0.0108(13) 0.0128(15) 0.0182(16) -0.0012(13) -0.0018(12) -0.0020(12) C232 0.0164(15) 0.0208(17) 0.0155(16) -0.0029(14) -0.0032(12) -0.0050(14) C233 0.0231(16) 0.0183(17) 0.0232(18) 0.0028(15) -0.0075(14) -0.0035(14) C234 0.0132(14) 0.0158(16) 0.0328(19) -0.0061(15) -0.0068(14) -0.0029(13) C235 0.0187(15) 0.0222(18) 0.0182(17) -0.0037(15) -0.0021(13) -0.0061(14) C236 0.0163(14) 0.0155(17) 0.0227(17) 0.0031(14) -0.0047(13) -0.0038(13) C241 0.0109(13) 0.0187(17) 0.0159(16) 0.0041(13) 0.0004(12) -0.0013(13) C242 0.0155(14) 0.0220(17) 0.0209(17) 0.0003(14) -0.0014(13) -0.0015(13) C243 0.0271(16) 0.036(2) 0.0158(17) -0.0048(15) -0.0030(14) 0.0021(15) C244 0.0312(17) 0.035(2) 0.0198(18) 0.0114(16) 0.0025(14) 0.0049(16) C245 0.0290(16) 0.0243(18) 0.0274(19) 0.0070(16) 0.0023(15) -0.0023(15) C246 0.0173(15) 0.0242(18) 0.0227(18) 0.0011(15) -0.0009(13) -0.0036(14) S1 0.0208(4) 0.0214(5) 0.0272(5) 0.0033(4) -0.0042(3) -0.0061(4) O11 0.0370(12) 0.0215(12) 0.0374(13) -0.0105(10) -0.0057(10) -0.0040(10) O12 0.0276(11) 0.0468(14) 0.0407(14) 0.0180(12) 0.0018(10) -0.0161(11) O13 0.0306(11) 0.0185(12) 0.0339(13) 0.0057(10) -0.0135(10) -0.0033(10) C1 0.0224(16) 0.0253(19) 0.0211(18) 0.0015(16) 0.0018(14) 0.0012(15) F11 0.0309(9) 0.0497(12) 0.0352(11) -0.0219(10) -0.0035(8) -0.0036(9) F12 0.0301(9) 0.0633(13) 0.0276(10) -0.0071(9) 0.0078(8) -0.0243(10) F13 0.0342(10) 0.0461(12) 0.0495(13) 0.0127(10) -0.0180(9) 0.0014(9) S2 0.0232(4) 0.0178(4) 0.0201(4) 0.0015(4) -0.0031(3) -0.0027(3) O21 0.0291(10) 0.0139(11) 0.0275(12) 0.0051(10) -0.0066(9) 0.0032(9) O22 0.0172(10) 0.0234(12) 0.0377(13) 0.0057(10) 0.0029(9) 0.0028(9) O23 0.0546(13) 0.0397(14) 0.0154(12) 0.0023(11) -0.0025(10) 0.0026(11) C2 0.039(2) 0.030(2) 0.038(2) 0.0133(18) -0.0095(17) -0.0133(17) F21 0.0694(12) 0.0234(11) 0.0629(14) 0.0143(10) -0.0172(10) -0.0180(10) F22 0.0308(11) 0.0665(15) 0.1066(18) 0.0218(13) -0.0031(11) -0.0244(11) F23 0.0990(15) 0.0505(13) 0.0415(13) 0.0065(11) -0.0298(11) -0.0445(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C131 1.795(3) . ? P1 C141 1.798(3) . ? P1 C121 1.804(2) . ? P1 C10 1.805(2) . ? C10 C111 1.528(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C111 C112 1.388(3) . ? C111 C116 1.388(3) . ? C112 C113 1.396(3) . ? C112 H112 0.9500 . ? C113 C114 1.382(4) . ? C113 H113 0.9500 . ? C114 C115 1.379(4) . ? C114 H114 0.9500 . ? C115 C116 1.386(3) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C122 1.389(3) . ? C121 C126 1.392(3) . ? C122 C123 1.385(3) . ? C122 H122 0.9500 . ? C123 C124 1.384(3) . ? C123 H123 0.9500 . ? C124 C125 1.385(3) . ? C124 H124 0.9500 . ? C125 C126 1.378(3) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C131 C132 1.390(3) . ? C131 C136 1.403(3) . ? C132 C133 1.385(4) . ? C132 H132 0.9500 . ? C133 C134 1.385(3) . ? C133 H133 0.9500 . ? C134 C135 1.379(4) . ? C134 H134 0.9500 . ? C135 C136 1.381(4) . ? C135 H135 0.9500 . ? C136 H136 0.9500 . ? C141 C146 1.384(4) . ? C141 C142 1.398(3) . ? C142 C143 1.386(4) . ? C142 H142 0.9500 . ? C143 C144 1.383(4) . ? C143 H143 0.9500 . ? C144 C145 1.380(3) . ? C144 H144 0.9500 . ? C145 C146 1.393(4) . ? C145 H145 0.9500 . ? C146 H146 0.9500 . ? P2 C221 1.789(2) . ? P2 C241 1.790(2) . ? P2 C231 1.792(3) . ? P2 C20 1.810(2) . ? C20 C211 1.514(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C211 C212 1.386(3) . ? C211 C216 1.388(3) . ? C212 C213 1.388(3) . ? C212 H212 0.9500 . ? C213 C214 1.375(4) . ? C213 H213 0.9500 . ? C214 C215 1.382(4) . ? C214 H214 0.9500 . ? C215 C216 1.384(3) . ? C215 H215 0.9500 . ? C216 H216 0.9500 . ? C221 C222 1.385(4) . ? C221 C226 1.401(3) . ? C222 C223 1.392(3) . ? C222 H222 0.9500 . ? C223 C224 1.385(3) . ? C223 H223 0.9500 . ? C224 C225 1.375(4) . ? C224 H224 0.9500 . ? C225 C226 1.385(3) . ? C225 H225 0.9500 . ? C226 H226 0.9500 . ? C231 C236 1.385(3) . ? C231 C232 1.396(3) . ? C232 C233 1.384(3) . ? C232 H232 0.9500 . ? C233 C234 1.383(4) . ? C233 H233 0.9500 . ? C234 C235 1.383(3) . ? C234 H234 0.9500 . ? C235 C236 1.387(3) . ? C235 H235 0.9500 . ? C236 H236 0.9500 . ? C241 C246 1.393(3) . ? C241 C242 1.396(3) . ? C242 C243 1.379(3) . ? C242 H242 0.9500 . ? C243 C244 1.389(4) . ? C243 H243 0.9500 . ? C244 C245 1.374(4) . ? C244 H244 0.9500 . ? C245 C246 1.380(3) . ? C245 H245 0.9500 . ? C246 H246 0.9500 . ? S1 O13 1.4371(17) . ? S1 O12 1.4382(17) . ? S1 O11 1.453(2) . ? S1 C1 1.817(3) . ? C1 F11 1.331(3) . ? C1 F12 1.333(3) . ? C1 F13 1.337(3) . ? S2 O22 1.4337(18) . ? S2 O23 1.4388(19) . ? S2 O21 1.4503(17) . ? S2 C2 1.812(3) . ? C2 F22 1.330(3) . ? C2 F23 1.332(3) . ? C2 F21 1.332(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C131 P1 C141 111.56(12) . . ? C131 P1 C121 107.11(11) . . ? C141 P1 C121 109.13(11) . . ? C131 P1 C10 111.94(12) . . ? C141 P1 C10 108.05(12) . . ? C121 P1 C10 108.99(11) . . ? C111 C10 P1 115.57(16) . . ? C111 C10 H10A 108.4 . . ? P1 C10 H10A 108.4 . . ? C111 C10 H10B 108.4 . . ? P1 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C112 C111 C116 118.9(2) . . ? C112 C111 C10 120.3(2) . . ? C116 C111 C10 120.6(2) . . ? C111 C112 C113 120.3(3) . . ? C111 C112 H112 119.9 . . ? C113 C112 H112 119.9 . . ? C114 C113 C112 120.1(3) . . ? C114 C113 H113 120.0 . . ? C112 C113 H113 120.0 . . ? C115 C114 C113 119.8(2) . . ? C115 C114 H114 120.1 . . ? C113 C114 H114 120.1 . . ? C114 C115 C116 120.2(3) . . ? C114 C115 H115 119.9 . . ? C116 C115 H115 119.9 . . ? C115 C116 C111 120.7(3) . . ? C115 C116 H116 119.6 . . ? C111 C116 H116 119.6 . . ? C122 C121 C126 119.5(2) . . ? C122 C121 P1 121.86(19) . . ? C126 C121 P1 118.54(18) . . ? C123 C122 C121 119.9(2) . . ? C123 C122 H122 120.1 . . ? C121 C122 H122 120.1 . . ? C124 C123 C122 120.7(2) . . ? C124 C123 H123 119.6 . . ? C122 C123 H123 119.6 . . ? C123 C124 C125 119.2(2) . . ? C123 C124 H124 120.4 . . ? C125 C124 H124 120.4 . . ? C126 C125 C124 120.8(2) . . ? C126 C125 H125 119.6 . . ? C124 C125 H125 119.6 . . ? C125 C126 C121 120.0(2) . . ? C125 C126 H126 120.0 . . ? C121 C126 H126 120.0 . . ? C132 C131 C136 119.7(3) . . ? C132 C131 P1 119.21(19) . . ? C136 C131 P1 120.7(2) . . ? C133 C132 C131 119.8(2) . . ? C133 C132 H132 120.1 . . ? C131 C132 H132 120.1 . . ? C132 C133 C134 120.1(3) . . ? C132 C133 H133 120.0 . . ? C134 C133 H133 120.0 . . ? C135 C134 C133 120.5(3) . . ? C135 C134 H134 119.8 . . ? C133 C134 H134 119.8 . . ? C134 C135 C136 120.1(3) . . ? C134 C135 H135 119.9 . . ? C136 C135 H135 119.9 . . ? C135 C136 C131 119.8(3) . . ? C135 C136 H136 120.1 . . ? C131 C136 H136 120.1 . . ? C146 C141 C142 121.2(3) . . ? C146 C141 P1 117.30(18) . . ? C142 C141 P1 121.0(2) . . ? C143 C142 C141 118.5(3) . . ? C143 C142 H142 120.8 . . ? C141 C142 H142 120.8 . . ? C144 C143 C142 120.8(2) . . ? C144 C143 H143 119.6 . . ? C142 C143 H143 119.6 . . ? C145 C144 C143 120.3(3) . . ? C145 C144 H144 119.8 . . ? C143 C144 H144 119.8 . . ? C144 C145 C146 120.0(3) . . ? C144 C145 H145 120.0 . . ? C146 C145 H145 120.0 . . ? C141 C146 C145 119.3(2) . . ? C141 C146 H146 120.4 . . ? C145 C146 H146 120.4 . . ? C221 P2 C241 108.50(11) . . ? C221 P2 C231 109.13(11) . . ? C241 P2 C231 110.62(12) . . ? C221 P2 C20 108.97(12) . . ? C241 P2 C20 109.69(11) . . ? C231 P2 C20 109.89(11) . . ? C211 C20 P2 111.76(17) . . ? C211 C20 H20A 109.3 . . ? P2 C20 H20A 109.3 . . ? C211 C20 H20B 109.3 . . ? P2 C20 H20B 109.3 . . ? H20A C20 H20B 107.9 . . ? C212 C211 C216 119.5(2) . . ? C212 C211 C20 121.5(2) . . ? C216 C211 C20 119.0(2) . . ? C211 C212 C213 119.9(3) . . ? C211 C212 H212 120.0 . . ? C213 C212 H212 120.0 . . ? C214 C213 C212 120.4(3) . . ? C214 C213 H213 119.8 . . ? C212 C213 H213 119.8 . . ? C213 C214 C215 119.9(3) . . ? C213 C214 H214 120.0 . . ? C215 C214 H214 120.0 . . ? C214 C215 C216 120.1(3) . . ? C214 C215 H215 120.0 . . ? C216 C215 H215 120.0 . . ? C215 C216 C211 120.2(3) . . ? C215 C216 H216 119.9 . . ? C211 C216 H216 119.9 . . ? C222 C221 C226 119.8(2) . . ? C222 C221 P2 120.83(18) . . ? C226 C221 P2 119.2(2) . . ? C221 C222 C223 120.2(2) . . ? C221 C222 H222 119.9 . . ? C223 C222 H222 119.9 . . ? C224 C223 C222 120.0(3) . . ? C224 C223 H223 120.0 . . ? C222 C223 H223 120.0 . . ? C225 C224 C223 119.7(2) . . ? C225 C224 H224 120.1 . . ? C223 C224 H224 120.1 . . ? C224 C225 C226 121.2(2) . . ? C224 C225 H225 119.4 . . ? C226 C225 H225 119.4 . . ? C225 C226 C221 119.1(3) . . ? C225 C226 H226 120.5 . . ? C221 C226 H226 120.5 . . ? C236 C231 C232 119.8(2) . . ? C236 C231 P2 122.28(19) . . ? C232 C231 P2 117.6(2) . . ? C233 C232 C231 119.7(3) . . ? C233 C232 H232 120.2 . . ? C231 C232 H232 120.2 . . ? C234 C233 C232 120.2(2) . . ? C234 C233 H233 119.9 . . ? C232 C233 H233 119.9 . . ? C233 C234 C235 120.4(3) . . ? C233 C234 H234 119.8 . . ? C235 C234 H234 119.8 . . ? C234 C235 C236 119.7(3) . . ? C234 C235 H235 120.1 . . ? C236 C235 H235 120.1 . . ? C231 C236 C235 120.2(2) . . ? C231 C236 H236 119.9 . . ? C235 C236 H236 119.9 . . ? C246 C241 C242 119.9(2) . . ? C246 C241 P2 119.5(2) . . ? C242 C241 P2 120.45(19) . . ? C243 C242 C241 119.5(2) . . ? C243 C242 H242 120.3 . . ? C241 C242 H242 120.3 . . ? C242 C243 C244 120.3(3) . . ? C242 C243 H243 119.9 . . ? C244 C243 H243 119.9 . . ? C245 C244 C243 120.2(3) . . ? C245 C244 H244 119.9 . . ? C243 C244 H244 119.9 . . ? C244 C245 C246 120.3(3) . . ? C244 C245 H245 119.9 . . ? C246 C245 H245 119.9 . . ? C245 C246 C241 119.9(3) . . ? C245 C246 H246 120.1 . . ? C241 C246 H246 120.1 . . ? O13 S1 O12 115.74(12) . . ? O13 S1 O11 115.16(11) . . ? O12 S1 O11 114.80(12) . . ? O13 S1 C1 103.08(11) . . ? O12 S1 C1 103.19(12) . . ? O11 S1 C1 102.15(12) . . ? F11 C1 F12 106.6(2) . . ? F11 C1 F13 106.9(2) . . ? F12 C1 F13 106.8(2) . . ? F11 C1 S1 112.95(19) . . ? F12 C1 S1 111.54(19) . . ? F13 C1 S1 111.70(18) . . ? O22 S2 O23 115.61(11) . . ? O22 S2 O21 114.42(10) . . ? O23 S2 O21 115.06(12) . . ? O22 S2 C2 103.09(14) . . ? O23 S2 C2 104.05(13) . . ? O21 S2 C2 102.10(12) . . ? F22 C2 F23 107.1(2) . . ? F22 C2 F21 107.0(2) . . ? F23 C2 F21 107.0(3) . . ? F22 C2 S2 112.1(2) . . ? F23 C2 S2 111.54(18) . . ? F21 C2 S2 111.8(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C131 P1 C10 C111 -62.1(2) . . . . ? C141 P1 C10 C111 61.1(2) . . . . ? C121 P1 C10 C111 179.6(2) . . . . ? P1 C10 C111 C112 112.9(2) . . . . ? P1 C10 C111 C116 -71.0(3) . . . . ? C116 C111 C112 C113 -1.2(4) . . . . ? C10 C111 C112 C113 175.0(2) . . . . ? C111 C112 C113 C114 1.1(4) . . . . ? C112 C113 C114 C115 -0.2(4) . . . . ? C113 C114 C115 C116 -0.7(4) . . . . ? C114 C115 C116 C111 0.7(4) . . . . ? C112 C111 C116 C115 0.3(4) . . . . ? C10 C111 C116 C115 -175.9(2) . . . . ? C131 P1 C121 C122 -119.0(2) . . . . ? C141 P1 C121 C122 120.1(2) . . . . ? C10 P1 C121 C122 2.3(3) . . . . ? C131 P1 C121 C126 57.5(2) . . . . ? C141 P1 C121 C126 -63.4(2) . . . . ? C10 P1 C121 C126 178.8(2) . . . . ? C126 C121 C122 C123 -1.5(4) . . . . ? P1 C121 C122 C123 174.9(2) . . . . ? C121 C122 C123 C124 0.6(4) . . . . ? C122 C123 C124 C125 0.3(4) . . . . ? C123 C124 C125 C126 -0.3(4) . . . . ? C124 C125 C126 C121 -0.6(4) . . . . ? C122 C121 C126 C125 1.5(4) . . . . ? P1 C121 C126 C125 -175.1(2) . . . . ? C141 P1 C131 C132 -149.02(18) . . . . ? C121 P1 C131 C132 91.6(2) . . . . ? C10 P1 C131 C132 -27.8(2) . . . . ? C141 P1 C131 C136 38.0(2) . . . . ? C121 P1 C131 C136 -81.4(2) . . . . ? C10 P1 C131 C136 159.20(18) . . . . ? C136 C131 C132 C133 0.1(3) . . . . ? P1 C131 C132 C133 -172.96(17) . . . . ? C131 C132 C133 C134 -0.5(3) . . . . ? C132 C133 C134 C135 0.5(4) . . . . ? C133 C134 C135 C136 -0.2(4) . . . . ? C134 C135 C136 C131 -0.2(3) . . . . ? C132 C131 C136 C135 0.2(3) . . . . ? P1 C131 C136 C135 173.18(18) . . . . ? C131 P1 C141 C146 -159.08(19) . . . . ? C121 P1 C141 C146 -40.9(2) . . . . ? C10 P1 C141 C146 77.5(2) . . . . ? C131 P1 C141 C142 29.2(2) . . . . ? C121 P1 C141 C142 147.34(19) . . . . ? C10 P1 C141 C142 -94.3(2) . . . . ? C146 C141 C142 C143 1.2(4) . . . . ? P1 C141 C142 C143 172.58(19) . . . . ? C141 C142 C143 C144 -1.1(4) . . . . ? C142 C143 C144 C145 -0.1(4) . . . . ? C143 C144 C145 C146 1.3(4) . . . . ? C142 C141 C146 C145 0.0(4) . . . . ? P1 C141 C146 C145 -171.72(18) . . . . ? C144 C145 C146 C141 -1.3(4) . . . . ? C221 P2 C20 C211 166.50(18) . . . . ? C241 P2 C20 C211 47.9(2) . . . . ? C231 P2 C20 C211 -74.0(2) . . . . ? P2 C20 C211 C212 89.6(3) . . . . ? P2 C20 C211 C216 -88.8(3) . . . . ? C216 C211 C212 C213 1.4(4) . . . . ? C20 C211 C212 C213 -177.0(2) . . . . ? C211 C212 C213 C214 0.5(4) . . . . ? C212 C213 C214 C215 -2.2(4) . . . . ? C213 C214 C215 C216 2.2(4) . . . . ? C214 C215 C216 C211 -0.3(4) . . . . ? C212 C211 C216 C215 -1.5(4) . . . . ? C20 C211 C216 C215 177.0(2) . . . . ? C241 P2 C221 C222 87.5(2) . . . . ? C231 P2 C221 C222 -151.9(2) . . . . ? C20 P2 C221 C222 -31.9(2) . . . . ? C241 P2 C221 C226 -86.8(2) . . . . ? C231 P2 C221 C226 33.8(2) . . . . ? C20 P2 C221 C226 153.84(19) . . . . ? C226 C221 C222 C223 0.5(4) . . . . ? P2 C221 C222 C223 -173.73(18) . . . . ? C221 C222 C223 C224 0.9(4) . . . . ? C222 C223 C224 C225 -1.5(4) . . . . ? C223 C224 C225 C226 0.8(4) . . . . ? C224 C225 C226 C221 0.6(4) . . . . ? C222 C221 C226 C225 -1.2(3) . . . . ? P2 C221 C226 C225 173.10(18) . . . . ? C221 P2 C231 C236 -104.1(2) . . . . ? C241 P2 C231 C236 15.2(2) . . . . ? C20 P2 C231 C236 136.48(18) . . . . ? C221 P2 C231 C232 69.16(18) . . . . ? C241 P2 C231 C232 -171.53(16) . . . . ? C20 P2 C231 C232 -50.27(19) . . . . ? C236 C231 C232 C233 -0.1(3) . . . . ? P2 C231 C232 C233 -173.57(16) . . . . ? C231 C232 C233 C234 0.0(3) . . . . ? C232 C233 C234 C235 -0.7(3) . . . . ? C233 C234 C235 C236 1.5(3) . . . . ? C232 C231 C236 C235 1.0(3) . . . . ? P2 C231 C236 C235 174.06(17) . . . . ? C234 C235 C236 C231 -1.6(3) . . . . ? C221 P2 C241 C246 -13.6(2) . . . . ? C231 P2 C241 C246 -133.30(19) . . . . ? C20 P2 C241 C246 105.3(2) . . . . ? C221 P2 C241 C242 170.7(2) . . . . ? C231 P2 C241 C242 51.1(2) . . . . ? C20 P2 C241 C242 -70.3(2) . . . . ? C246 C241 C242 C243 0.4(4) . . . . ? P2 C241 C242 C243 176.02(19) . . . . ? C241 C242 C243 C244 -0.8(4) . . . . ? C242 C243 C244 C245 1.2(4) . . . . ? C243 C244 C245 C246 -1.2(4) . . . . ? C244 C245 C246 C241 0.8(4) . . . . ? C242 C241 C246 C245 -0.4(4) . . . . ? P2 C241 C246 C245 -176.1(2) . . . . ? O13 S1 C1 F11 55.1(2) . . . . ? O12 S1 C1 F11 -65.7(2) . . . . ? O11 S1 C1 F11 174.89(18) . . . . ? O13 S1 C1 F12 -65.0(2) . . . . ? O12 S1 C1 F12 174.2(2) . . . . ? O11 S1 C1 F12 54.8(2) . . . . ? O13 S1 C1 F13 175.6(2) . . . . ? O12 S1 C1 F13 54.8(2) . . . . ? O11 S1 C1 F13 -64.6(2) . . . . ? O22 S2 C2 F22 -177.0(2) . . . . ? O23 S2 C2 F22 -56.0(2) . . . . ? O21 S2 C2 F22 64.0(2) . . . . ? O22 S2 C2 F23 62.9(2) . . . . ? O23 S2 C2 F23 -176.1(2) . . . . ? O21 S2 C2 F23 -56.0(2) . . . . ? O22 S2 C2 F21 -56.9(2) . . . . ? O23 S2 C2 F21 64.2(3) . . . . ? O21 S2 C2 F21 -175.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.293 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.058 # Attachment 'Complex_6.cif' data_230708c _database_code_depnum_ccdc_archive 'CCDC 760643' #TrackingRef 'Complex_6.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H38 P2, 2(C2 N3)' _chemical_formula_sum 'C48 H38 N6 P2' _chemical_formula_weight 760.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9176(4) _cell_length_b 13.7706(6) _cell_length_c 14.1618(6) _cell_angle_alpha 90.0 _cell_angle_beta 96.951(4) _cell_angle_gamma 90.0 _cell_volume 1919.88(14) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13611 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 32.49 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method ? _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96685 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55499 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 32.60 _reflns_number_total 6772 _reflns_number_gt 5191 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_cell_refinement ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_data_reduction ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET) (compiled Jan 10 2008,16:37:18) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0820P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6772 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1186 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.20421(3) 0.448641(17) 0.259490(17) 0.01212(7) Uani 1 1 d . . . C11 C 0.24131(10) 0.36367(7) 0.35536(7) 0.01453(18) Uani 1 1 d . . . C12 C 0.14224(11) 0.29601(7) 0.37401(7) 0.0176(2) Uani 1 1 d . . . H12 H 0.0563 0.2954 0.3362 0.021 Uiso 1 1 calc R . . C13 C 0.17011(12) 0.22995(7) 0.44789(8) 0.0211(2) Uani 1 1 d . . . H13 H 0.1028 0.1845 0.4610 0.025 Uiso 1 1 calc R . . C14 C 0.29605(12) 0.23013(8) 0.50264(8) 0.0221(2) Uani 1 1 d . . . H14 H 0.3149 0.1846 0.5529 0.027 Uiso 1 1 calc R . . C15 C 0.39424(12) 0.29671(9) 0.48403(8) 0.0235(2) Uani 1 1 d . . . H15 H 0.4803 0.2964 0.5217 0.028 Uiso 1 1 calc R . . C16 C 0.36797(11) 0.36406(8) 0.41065(7) 0.0191(2) Uani 1 1 d . . . H16 H 0.4355 0.4098 0.3983 0.023 Uiso 1 1 calc R . . C21 C 0.36013(10) 0.49728(7) 0.22817(7) 0.01455(19) Uani 1 1 d . . . C22 C 0.42933(11) 0.45039(8) 0.16074(8) 0.0176(2) Uani 1 1 d . . . H22 H 0.3916 0.3943 0.1285 0.021 Uiso 1 1 calc R . . C23 C 0.55410(11) 0.48680(8) 0.14140(8) 0.0222(2) Uani 1 1 d . . . H23 H 0.6011 0.4560 0.0950 0.027 Uiso 1 1 calc R . . C24 C 0.61003(11) 0.56783(8) 0.18953(8) 0.0226(2) Uani 1 1 d . . . H24 H 0.6952 0.5923 0.1759 0.027 Uiso 1 1 calc R . . C25 C 0.54219(11) 0.61346(8) 0.25756(8) 0.0205(2) Uani 1 1 d . . . H25 H 0.5816 0.6684 0.2908 0.025 Uiso 1 1 calc R . . C26 C 0.41680(10) 0.57884(7) 0.27707(7) 0.0174(2) Uani 1 1 d . . . H26 H 0.3700 0.6102 0.3232 0.021 Uiso 1 1 calc R . . C31 C 0.09966(10) 0.54525(7) 0.29303(7) 0.01290(18) Uani 1 1 d . . . C32 C 0.08772(10) 0.63043(7) 0.23809(7) 0.01596(19) Uani 1 1 d . . . H32 H 0.1438 0.6401 0.1891 0.019 Uiso 1 1 calc R . . C33 C -0.00670(11) 0.70017(7) 0.25603(7) 0.0176(2) Uani 1 1 d . . . H33 H -0.0153 0.7580 0.2192 0.021 Uiso 1 1 calc R . . C34 C -0.08880(11) 0.68596(7) 0.32775(7) 0.0184(2) Uani 1 1 d . . . H34 H -0.1533 0.7341 0.3395 0.022 Uiso 1 1 calc R . . C35 C -0.07708(11) 0.60189(7) 0.38226(8) 0.0184(2) Uani 1 1 d . . . H35 H -0.1335 0.5926 0.4311 0.022 Uiso 1 1 calc R . . C36 C 0.01724(10) 0.53133(7) 0.36533(7) 0.01546(19) Uani 1 1 d . . . H36 H 0.0257 0.4739 0.4027 0.019 Uiso 1 1 calc R . . C40 C 0.11280(10) 0.38226(7) 0.16166(7) 0.01374(18) Uani 1 1 d . . . H401 H 0.1747 0.3334 0.1390 0.016 Uiso 1 1 calc R . . H402 H 0.0369 0.3468 0.1855 0.016 Uiso 1 1 calc R . . C41 C 0.05588(10) 0.44448(6) 0.07819(7) 0.01271(18) Uani 1 1 d . . . C42 C -0.06639(10) 0.49420(7) 0.08056(7) 0.01463(19) Uani 1 1 d . . . H42 H -0.1120 0.4904 0.1357 0.018 Uiso 1 1 calc R . . C43 C -0.12233(10) 0.54929(7) 0.00313(7) 0.01426(18) Uani 1 1 d . . . H43 H -0.2057 0.5827 0.0056 0.017 Uiso 1 1 calc R . . N1 N 0.73311(13) 0.38547(8) 0.40308(8) 0.0361(3) Uani 1 1 d . . . C10 C 0.75166(13) 0.32448(9) 0.47446(9) 0.0300(3) Uani 1 1 d . . . C20 C 0.78118(11) 0.36316(8) 0.32364(8) 0.0205(2) Uani 1 1 d . . . N10 N 0.76177(14) 0.27587(10) 0.54184(8) 0.0451(3) Uani 1 1 d . . . N20 N 0.82092(10) 0.35041(7) 0.25082(7) 0.0229(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01239(12) 0.01293(12) 0.01104(12) 0.00017(8) 0.00140(9) 0.00088(8) C11 0.0166(5) 0.0154(4) 0.0118(4) 0.0003(3) 0.0023(3) 0.0037(3) C12 0.0206(5) 0.0166(4) 0.0153(5) 0.0009(4) 0.0011(4) 0.0014(4) C13 0.0276(6) 0.0169(5) 0.0194(5) 0.0046(4) 0.0045(4) 0.0028(4) C14 0.0291(6) 0.0216(5) 0.0159(5) 0.0045(4) 0.0038(4) 0.0098(4) C15 0.0214(5) 0.0315(6) 0.0168(5) 0.0031(4) -0.0007(4) 0.0080(4) C16 0.0171(5) 0.0234(5) 0.0167(5) 0.0008(4) 0.0012(4) 0.0025(4) C21 0.0130(4) 0.0166(4) 0.0141(4) 0.0016(3) 0.0018(3) 0.0015(3) C22 0.0148(5) 0.0205(5) 0.0175(5) -0.0017(4) 0.0022(4) 0.0019(4) C23 0.0167(5) 0.0287(5) 0.0221(5) -0.0022(4) 0.0062(4) 0.0022(4) C24 0.0142(5) 0.0281(5) 0.0259(6) 0.0014(4) 0.0040(4) -0.0011(4) C25 0.0167(5) 0.0201(5) 0.0247(5) -0.0015(4) 0.0018(4) -0.0028(4) C26 0.0161(5) 0.0178(4) 0.0182(5) -0.0012(4) 0.0025(4) -0.0002(4) C31 0.0128(4) 0.0130(4) 0.0129(4) -0.0011(3) 0.0016(3) 0.0002(3) C32 0.0168(5) 0.0161(4) 0.0154(4) 0.0008(3) 0.0034(4) 0.0003(4) C33 0.0189(5) 0.0149(4) 0.0188(5) 0.0019(4) 0.0022(4) 0.0018(4) C34 0.0168(5) 0.0182(5) 0.0204(5) -0.0005(4) 0.0037(4) 0.0043(4) C35 0.0183(5) 0.0199(5) 0.0178(5) -0.0002(4) 0.0059(4) 0.0022(4) C36 0.0158(5) 0.0159(4) 0.0151(4) 0.0005(3) 0.0034(4) 0.0003(4) C40 0.0160(4) 0.0135(4) 0.0116(4) 0.0001(3) 0.0013(3) -0.0003(3) C41 0.0137(4) 0.0131(4) 0.0110(4) -0.0006(3) -0.0001(3) -0.0013(3) C42 0.0142(4) 0.0177(4) 0.0122(4) -0.0002(3) 0.0028(3) -0.0001(3) C43 0.0122(4) 0.0172(4) 0.0134(4) -0.0005(3) 0.0019(3) 0.0010(3) N1 0.0511(7) 0.0311(6) 0.0299(6) 0.0039(4) 0.0201(5) 0.0057(5) C10 0.0325(7) 0.0334(6) 0.0252(6) -0.0034(5) 0.0078(5) -0.0162(5) C20 0.0171(5) 0.0192(5) 0.0251(5) 0.0038(4) 0.0018(4) -0.0016(4) N10 0.0558(8) 0.0536(8) 0.0245(6) 0.0063(5) -0.0006(5) -0.0335(7) N20 0.0218(5) 0.0241(5) 0.0229(5) 0.0013(4) 0.0034(4) -0.0043(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C31 1.7860(10) . ? P1 C21 1.7895(10) . ? P1 C11 1.7963(10) . ? P1 C40 1.8092(10) . ? C11 C16 1.3975(14) . ? C11 C12 1.4022(14) . ? C12 C13 1.3888(14) . ? C12 H12 0.9500 . ? C13 C14 1.3882(16) . ? C13 H13 0.9500 . ? C14 C15 1.3858(17) . ? C14 H14 0.9500 . ? C15 C16 1.3938(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.3994(14) . ? C21 C26 1.4010(14) . ? C22 C23 1.3926(15) . ? C22 H22 0.9500 . ? C23 C24 1.3878(16) . ? C23 H23 0.9500 . ? C24 C25 1.3903(16) . ? C24 H24 0.9500 . ? C25 C26 1.3904(15) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.3985(14) . ? C31 C32 1.4045(13) . ? C32 C33 1.3862(14) . ? C32 H32 0.9500 . ? C33 C34 1.3903(14) . ? C33 H33 0.9500 . ? C34 C35 1.3885(14) . ? C34 H34 0.9500 . ? C35 C36 1.3896(14) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C40 C41 1.5128(13) . ? C40 H401 0.9900 . ? C40 H402 0.9900 . ? C41 C42 1.3965(14) . ? C41 C43 1.3969(14) 3_565 ? C42 C43 1.3924(13) . ? C42 H42 0.9500 . ? C43 C41 1.3969(14) 3_565 ? C43 H43 0.9500 . ? N1 C10 1.3100(17) . ? N1 C20 1.3104(16) . ? C10 N10 1.1600(17) . ? C20 N20 1.1611(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C31 P1 C21 109.51(4) . . ? C31 P1 C11 110.89(5) . . ? C21 P1 C11 109.09(5) . . ? C31 P1 C40 109.07(5) . . ? C21 P1 C40 111.54(5) . . ? C11 P1 C40 106.71(5) . . ? C16 C11 C12 119.99(9) . . ? C16 C11 P1 120.60(8) . . ? C12 C11 P1 119.41(8) . . ? C13 C12 C11 119.81(10) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.21(10) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.03(10) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.65(10) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.31(10) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C22 C21 C26 120.44(9) . . ? C22 C21 P1 120.42(8) . . ? C26 C21 P1 118.98(7) . . ? C23 C22 C21 119.27(10) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C24 C23 C22 120.32(10) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 120.37(10) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 120.14(10) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 119.45(10) . . ? C25 C26 H26 120.3 . . ? C21 C26 H26 120.3 . . ? C36 C31 C32 120.16(9) . . ? C36 C31 P1 120.14(7) . . ? C32 C31 P1 119.17(7) . . ? C33 C32 C31 119.38(9) . . ? C33 C32 H32 120.3 . . ? C31 C32 H32 120.3 . . ? C32 C33 C34 120.31(9) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C35 C34 C33 120.43(9) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 120.00(10) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 119.72(9) . . ? C35 C36 H36 120.1 . . ? C31 C36 H36 120.1 . . ? C41 C40 P1 114.66(6) . . ? C41 C40 H401 108.6 . . ? P1 C40 H401 108.6 . . ? C41 C40 H402 108.6 . . ? P1 C40 H402 108.6 . . ? H401 C40 H402 107.6 . . ? C42 C41 C43 119.18(9) . 3_565 ? C42 C41 C40 120.12(9) . . ? C43 C41 C40 120.68(9) 3_565 . ? C43 C42 C41 120.83(9) . . ? C43 C42 H42 119.6 . . ? C41 C42 H42 119.6 . . ? C42 C43 C41 119.99(9) . 3_565 ? C42 C43 H43 120.0 . . ? C41 C43 H43 120.0 3_565 . ? C10 N1 C20 118.72(11) . . ? N10 C10 N1 174.19(16) . . ? N20 C20 N1 174.80(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C31 P1 C11 C16 -102.79(9) . . . . ? C21 P1 C11 C16 17.90(10) . . . . ? C40 P1 C11 C16 138.54(8) . . . . ? C31 P1 C11 C12 77.73(9) . . . . ? C21 P1 C11 C12 -161.58(8) . . . . ? C40 P1 C11 C12 -40.94(9) . . . . ? C16 C11 C12 C13 0.42(15) . . . . ? P1 C11 C12 C13 179.90(8) . . . . ? C11 C12 C13 C14 -0.61(16) . . . . ? C12 C13 C14 C15 0.36(16) . . . . ? C13 C14 C15 C16 0.10(16) . . . . ? C14 C15 C16 C11 -0.29(16) . . . . ? C12 C11 C16 C15 0.03(15) . . . . ? P1 C11 C16 C15 -179.45(8) . . . . ? C31 P1 C21 C22 -150.08(8) . . . . ? C11 P1 C21 C22 88.39(9) . . . . ? C40 P1 C21 C22 -29.24(10) . . . . ? C31 P1 C21 C26 34.52(9) . . . . ? C11 P1 C21 C26 -87.01(9) . . . . ? C40 P1 C21 C26 155.36(8) . . . . ? C26 C21 C22 C23 -1.23(16) . . . . ? P1 C21 C22 C23 -176.55(8) . . . . ? C21 C22 C23 C24 0.95(17) . . . . ? C22 C23 C24 C25 0.04(18) . . . . ? C23 C24 C25 C26 -0.77(17) . . . . ? C24 C25 C26 C21 0.50(16) . . . . ? C22 C21 C26 C25 0.51(15) . . . . ? P1 C21 C26 C25 175.90(8) . . . . ? C21 P1 C31 C36 -144.58(8) . . . . ? C11 P1 C31 C36 -24.13(10) . . . . ? C40 P1 C31 C36 93.10(9) . . . . ? C21 P1 C31 C32 43.68(9) . . . . ? C11 P1 C31 C32 164.12(8) . . . . ? C40 P1 C31 C32 -78.65(9) . . . . ? C36 C31 C32 C33 -0.22(15) . . . . ? P1 C31 C32 C33 171.52(8) . . . . ? C31 C32 C33 C34 0.01(15) . . . . ? C32 C33 C34 C35 0.09(16) . . . . ? C33 C34 C35 C36 0.04(16) . . . . ? C34 C35 C36 C31 -0.26(15) . . . . ? C32 C31 C36 C35 0.35(15) . . . . ? P1 C31 C36 C35 -171.31(8) . . . . ? C31 P1 C40 C41 52.39(8) . . . . ? C21 P1 C40 C41 -68.70(8) . . . . ? C11 P1 C40 C41 172.24(7) . . . . ? P1 C40 C41 C42 -81.26(10) . . . . ? P1 C40 C41 C43 100.67(9) . . . 3_565 ? C43 C41 C42 C43 0.14(15) 3_565 . . . ? C40 C41 C42 C43 -177.95(9) . . . . ? C41 C42 C43 C41 -0.14(15) . . . 3_565 ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 31.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.452 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.062 # Attachment 'Complex_7.cif' data_230708f _database_code_depnum_ccdc_archive 'CCDC 760644' #TrackingRef 'Complex_7.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H38 P2, 2(C4 N3)' _chemical_formula_sum 'C52 H38 N6 P2' _chemical_formula_weight 808.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8685(2) _cell_length_b 14.9561(4) _cell_length_c 14.2387(4) _cell_angle_alpha 90.0 _cell_angle_beta 97.885(2) _cell_angle_gamma 90.0 _cell_volume 2081.68(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8340 _cell_measurement_theta_min 3.59 _cell_measurement_theta_max 32.65 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method ? _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 0.150 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.99206 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24576 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 32.74 _reflns_number_total 7053 _reflns_number_gt 4680 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7053 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.71408(3) 0.054897(19) 0.25838(2) 0.01365(7) Uani 1 1 d . . . C10 C 0.62819(11) 0.11235(7) 0.15429(8) 0.0156(2) Uani 1 1 d . . . H10A H 0.5561 0.1511 0.1743 0.019 Uiso 1 1 calc R . . H10B H 0.6954 0.1517 0.1292 0.019 Uiso 1 1 calc R . . C11 C 0.75003(11) 0.13914(7) 0.34836(8) 0.0151(2) Uani 1 1 d . . . C12 C 0.65325(12) 0.20462(8) 0.36100(8) 0.0200(2) Uani 1 1 d . . . H12 H 0.5672 0.2048 0.3218 0.024 Uiso 1 1 calc R . . C13 C 0.68225(13) 0.26939(8) 0.43058(9) 0.0235(3) Uani 1 1 d . . . H13 H 0.6162 0.3137 0.4393 0.028 Uiso 1 1 calc R . . C14 C 0.80856(14) 0.26900(8) 0.48740(8) 0.0240(3) Uani 1 1 d . . . H14 H 0.8285 0.3130 0.5354 0.029 Uiso 1 1 calc R . . C15 C 0.90496(13) 0.20514(9) 0.47441(9) 0.0251(3) Uani 1 1 d . . . H15 H 0.9916 0.2061 0.5128 0.030 Uiso 1 1 calc R . . C16 C 0.87658(12) 0.13935(8) 0.40568(8) 0.0201(2) Uani 1 1 d . . . H16 H 0.9428 0.0949 0.3978 0.024 Uiso 1 1 calc R . . C21 C 0.60542(11) -0.03191(7) 0.29263(8) 0.0148(2) Uani 1 1 d . . . C22 C 0.52278(11) -0.01872(8) 0.36362(8) 0.0172(2) Uani 1 1 d . . . H22 H 0.5254 0.0366 0.3965 0.021 Uiso 1 1 calc R . . C23 C 0.43681(12) -0.08666(8) 0.38603(8) 0.0206(3) Uani 1 1 d . . . H23 H 0.3806 -0.0777 0.4343 0.025 Uiso 1 1 calc R . . C24 C 0.43266(12) -0.16752(8) 0.33824(8) 0.0213(3) Uani 1 1 d . . . H24 H 0.3746 -0.2141 0.3544 0.026 Uiso 1 1 calc R . . C25 C 0.51307(13) -0.18053(8) 0.26705(9) 0.0237(3) Uani 1 1 d . . . H25 H 0.5091 -0.2358 0.2340 0.028 Uiso 1 1 calc R . . C26 C 0.59944(12) -0.11342(8) 0.24372(9) 0.0208(2) Uani 1 1 d . . . H26 H 0.6543 -0.1227 0.1947 0.025 Uiso 1 1 calc R . . C31 C 0.87103(11) 0.00478(8) 0.23467(8) 0.0161(2) Uani 1 1 d . . . C32 C 0.94046(12) 0.03916(8) 0.16361(8) 0.0208(3) Uani 1 1 d . . . H32 H 0.9033 0.0880 0.1259 0.025 Uiso 1 1 calc R . . C33 C 1.06453(12) 0.00139(9) 0.14834(9) 0.0262(3) Uani 1 1 d . . . H33 H 1.1118 0.0242 0.0997 0.031 Uiso 1 1 calc R . . C34 C 1.11923(12) -0.06918(9) 0.20367(9) 0.0246(3) Uani 1 1 d . . . H34 H 1.2035 -0.0951 0.1925 0.030 Uiso 1 1 calc R . . C35 C 1.05194(13) -0.10227(9) 0.27525(9) 0.0242(3) Uani 1 1 d . . . H35 H 1.0909 -0.1501 0.3137 0.029 Uiso 1 1 calc R . . C36 C 0.92755(12) -0.06591(8) 0.29116(8) 0.0205(2) Uani 1 1 d . . . H36 H 0.8812 -0.0890 0.3402 0.025 Uiso 1 1 calc R . . C41 C 0.56343(11) 0.05267(7) 0.07465(7) 0.0135(2) Uani 1 1 d . . . C42 C 0.43465(11) 0.01550(8) 0.07876(8) 0.0164(2) Uani 1 1 d . . . H42 H 0.3896 0.0260 0.1325 0.020 Uiso 1 1 calc R . . C43 C 0.37204(11) -0.03681(7) 0.00460(8) 0.0162(2) Uani 1 1 d . . . H43 H 0.2845 -0.0619 0.0081 0.019 Uiso 1 1 calc R . . C0 C 0.28124(12) 0.16621(8) 0.40133(8) 0.0208(2) Uani 1 1 d . . . C1 C 0.29713(11) 0.16647(8) 0.30456(9) 0.0190(2) Uani 1 1 d . . . C2 C 0.32430(13) 0.24072(9) 0.45838(9) 0.0247(3) Uani 1 1 d . . . C3 C 0.22633(12) 0.09215(9) 0.44431(9) 0.0240(3) Uani 1 1 d . . . N1 N 0.31484(10) 0.16854(7) 0.22615(7) 0.0236(2) Uani 1 1 d . . . N2 N 0.36019(13) 0.30084(8) 0.50574(8) 0.0366(3) Uani 1 1 d . . . N3 N 0.18093(12) 0.03306(9) 0.48166(9) 0.0357(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01355(13) 0.01549(14) 0.01182(13) -0.00108(11) 0.00137(10) -0.00012(12) C10 0.0161(5) 0.0159(5) 0.0142(5) -0.0010(4) 0.0006(4) 0.0003(4) C11 0.0176(5) 0.0162(5) 0.0118(5) -0.0010(4) 0.0028(4) -0.0039(4) C12 0.0183(5) 0.0225(6) 0.0187(6) -0.0038(5) 0.0007(5) -0.0010(5) C13 0.0265(6) 0.0209(6) 0.0237(6) -0.0065(5) 0.0059(5) -0.0007(5) C14 0.0329(7) 0.0221(6) 0.0167(6) -0.0049(5) 0.0028(5) -0.0093(6) C15 0.0254(6) 0.0287(7) 0.0190(6) -0.0024(5) -0.0044(5) -0.0053(6) C16 0.0202(6) 0.0223(6) 0.0169(6) -0.0001(5) -0.0008(5) -0.0005(5) C21 0.0134(5) 0.0163(5) 0.0141(5) 0.0003(4) 0.0003(4) -0.0003(4) C22 0.0173(5) 0.0189(6) 0.0151(5) -0.0021(4) 0.0010(4) 0.0010(5) C23 0.0176(5) 0.0278(6) 0.0168(6) 0.0012(5) 0.0039(5) -0.0001(5) C24 0.0192(6) 0.0222(6) 0.0218(6) 0.0039(5) -0.0002(5) -0.0040(5) C25 0.0266(6) 0.0170(6) 0.0269(7) -0.0034(5) 0.0016(5) -0.0026(5) C26 0.0225(6) 0.0210(6) 0.0196(6) -0.0039(5) 0.0056(5) 0.0005(5) C31 0.0136(5) 0.0193(6) 0.0149(5) -0.0027(4) 0.0007(4) 0.0001(4) C32 0.0163(5) 0.0262(7) 0.0197(6) 0.0037(5) 0.0018(5) 0.0006(5) C33 0.0174(6) 0.0400(8) 0.0224(6) 0.0033(6) 0.0068(5) 0.0003(6) C34 0.0161(5) 0.0338(7) 0.0239(6) -0.0045(5) 0.0022(5) 0.0061(5) C35 0.0228(6) 0.0252(6) 0.0241(6) 0.0015(5) 0.0011(5) 0.0068(5) C36 0.0203(6) 0.0239(6) 0.0179(6) 0.0016(5) 0.0039(5) 0.0019(5) C41 0.0137(5) 0.0136(5) 0.0125(5) 0.0008(4) -0.0009(4) 0.0024(4) C42 0.0156(5) 0.0205(6) 0.0134(5) -0.0010(4) 0.0037(4) 0.0011(5) C43 0.0134(5) 0.0200(6) 0.0150(5) 0.0015(4) 0.0016(4) -0.0009(4) C0 0.0218(6) 0.0238(6) 0.0170(6) -0.0002(5) 0.0037(5) 0.0035(5) C1 0.0159(5) 0.0177(6) 0.0230(6) -0.0007(5) 0.0009(5) 0.0030(5) C2 0.0279(7) 0.0277(7) 0.0184(6) 0.0008(5) 0.0028(5) 0.0116(6) C3 0.0185(6) 0.0334(7) 0.0201(6) 0.0018(5) 0.0020(5) 0.0059(5) N1 0.0250(5) 0.0252(6) 0.0204(5) -0.0008(4) 0.0023(4) 0.0035(5) N2 0.0472(8) 0.0320(6) 0.0286(6) -0.0085(5) -0.0025(6) 0.0132(6) N3 0.0288(6) 0.0434(7) 0.0350(7) 0.0118(6) 0.0051(5) -0.0002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.7935(11) . ? P1 C31 1.7939(12) . ? P1 C11 1.7972(11) . ? P1 C10 1.8190(11) . ? C10 C41 1.5139(15) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3950(15) . ? C11 C12 1.3968(16) . ? C12 C13 1.3870(16) . ? C12 H12 0.9500 . ? C13 C14 1.3899(17) . ? C13 H13 0.9500 . ? C14 C15 1.3783(18) . ? C14 H14 0.9500 . ? C15 C16 1.3890(16) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.3971(16) . ? C21 C26 1.4013(16) . ? C22 C23 1.3886(17) . ? C22 H22 0.9500 . ? C23 C24 1.3855(17) . ? C23 H23 0.9500 . ? C24 C25 1.3841(18) . ? C24 H24 0.9500 . ? C25 C26 1.3864(17) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.3957(16) . ? C31 C36 1.3974(16) . ? C32 C33 1.3923(17) . ? C32 H32 0.9500 . ? C33 C34 1.3818(18) . ? C33 H33 0.9500 . ? C34 C35 1.3821(18) . ? C34 H34 0.9500 . ? C35 C36 1.3893(17) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C43 1.3899(15) 3_655 ? C41 C42 1.3957(15) . ? C42 C43 1.3893(15) . ? C42 H42 0.9500 . ? C43 C41 1.3899(15) 3_655 ? C43 H43 0.9500 . ? C0 C1 1.4080(17) . ? C0 C3 1.4092(18) . ? C0 C2 1.4099(18) . ? C1 N1 1.1540(15) . ? C2 N2 1.1502(16) . ? C3 N3 1.1533(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C31 108.22(5) . . ? C21 P1 C11 112.36(5) . . ? C31 P1 C11 109.63(5) . . ? C21 P1 C10 109.54(5) . . ? C31 P1 C10 111.22(5) . . ? C11 P1 C10 105.91(5) . . ? C41 C10 P1 115.68(8) . . ? C41 C10 H10A 108.4 . . ? P1 C10 H10A 108.4 . . ? C41 C10 H10B 108.4 . . ? P1 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C16 C11 C12 119.74(10) . . ? C16 C11 P1 119.47(9) . . ? C12 C11 P1 120.79(8) . . ? C13 C12 C11 120.27(11) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.57(12) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.35(11) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 120.61(11) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.45(11) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C22 C21 C26 119.57(11) . . ? C22 C21 P1 121.65(9) . . ? C26 C21 P1 118.72(9) . . ? C23 C22 C21 119.91(11) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.25(11) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 120.08(11) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.45(11) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 119.74(11) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C32 C31 C36 119.94(11) . . ? C32 C31 P1 120.33(9) . . ? C36 C31 P1 119.64(9) . . ? C33 C32 C31 119.57(11) . . ? C33 C32 H32 120.2 . . ? C31 C32 H32 120.2 . . ? C34 C33 C32 120.27(12) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 120.28(12) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C34 C35 C36 120.31(12) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C31 119.62(12) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C43 C41 C42 119.16(10) 3_655 . ? C43 C41 C10 121.02(10) 3_655 . ? C42 C41 C10 119.78(10) . . ? C43 C42 C41 120.33(10) . . ? C43 C42 H42 119.8 . . ? C41 C42 H42 119.8 . . ? C42 C43 C41 120.51(10) . 3_655 ? C42 C43 H43 119.7 . . ? C41 C43 H43 119.7 3_655 . ? C1 C0 C3 121.88(11) . . ? C1 C0 C2 119.76(11) . . ? C3 C0 C2 118.33(11) . . ? N1 C1 C0 177.32(13) . . ? N2 C2 C0 179.18(14) . . ? N3 C3 C0 178.05(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C10 C41 -47.42(10) . . . . ? C31 P1 C10 C41 72.15(10) . . . . ? C11 P1 C10 C41 -168.81(8) . . . . ? C21 P1 C11 C16 102.63(10) . . . . ? C31 P1 C11 C16 -17.74(11) . . . . ? C10 P1 C11 C16 -137.82(9) . . . . ? C21 P1 C11 C12 -77.86(10) . . . . ? C31 P1 C11 C12 161.77(9) . . . . ? C10 P1 C11 C12 41.69(11) . . . . ? C16 C11 C12 C13 -0.38(18) . . . . ? P1 C11 C12 C13 -179.89(9) . . . . ? C11 C12 C13 C14 0.31(18) . . . . ? C12 C13 C14 C15 0.47(19) . . . . ? C13 C14 C15 C16 -1.19(19) . . . . ? C14 C15 C16 C11 1.11(18) . . . . ? C12 C11 C16 C15 -0.33(17) . . . . ? P1 C11 C16 C15 179.19(9) . . . . ? C31 P1 C21 C22 141.84(9) . . . . ? C11 P1 C21 C22 20.66(11) . . . . ? C10 P1 C21 C22 -96.76(10) . . . . ? C31 P1 C21 C26 -41.00(10) . . . . ? C11 P1 C21 C26 -162.19(9) . . . . ? C10 P1 C21 C26 80.40(10) . . . . ? C26 C21 C22 C23 0.82(16) . . . . ? P1 C21 C22 C23 177.95(8) . . . . ? C21 C22 C23 C24 0.01(17) . . . . ? C22 C23 C24 C25 -0.80(17) . . . . ? C23 C24 C25 C26 0.76(18) . . . . ? C24 C25 C26 C21 0.07(18) . . . . ? C22 C21 C26 C25 -0.86(17) . . . . ? P1 C21 C26 C25 -178.07(9) . . . . ? C21 P1 C31 C32 145.70(9) . . . . ? C11 P1 C31 C32 -91.44(10) . . . . ? C10 P1 C31 C32 25.35(11) . . . . ? C21 P1 C31 C36 -37.79(10) . . . . ? C11 P1 C31 C36 85.07(10) . . . . ? C10 P1 C31 C36 -158.15(9) . . . . ? C36 C31 C32 C33 1.30(18) . . . . ? P1 C31 C32 C33 177.80(9) . . . . ? C31 C32 C33 C34 -0.56(19) . . . . ? C32 C33 C34 C35 -0.65(19) . . . . ? C33 C34 C35 C36 1.10(19) . . . . ? C34 C35 C36 C31 -0.35(18) . . . . ? C32 C31 C36 C35 -0.85(17) . . . . ? P1 C31 C36 C35 -177.37(9) . . . . ? P1 C10 C41 C43 -100.69(11) . . . 3_655 ? P1 C10 C41 C42 81.74(12) . . . . ? C43 C41 C42 C43 0.12(18) 3_655 . . . ? C10 C41 C42 C43 177.74(10) . . . . ? C41 C42 C43 C41 -0.12(18) . . . 3_655 ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.408 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.052 # Attachment 'Complex_8a.cif' data_170608n1#2 _database_code_depnum_ccdc_archive 'CCDC 760645' #TrackingRef 'Complex_8a.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H38 P2, 2(C2 F6 N O4 S2)' _chemical_formula_sum 'C48 H38 F12 N2 O8 P2 S4' _chemical_formula_weight 1188.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5923(5) _cell_length_b 11.4243(6) _cell_length_c 12.2741(6) _cell_angle_alpha 107.982(5) _cell_angle_beta 90.275(4) _cell_angle_gamma 101.322(4) _cell_volume 1251.37(11) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6550 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 31.8 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method ? _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 0.355 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini-R Ultra, Ruby CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.4738 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15083 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 31.91 _reflns_number_total 7654 _reflns_number_gt 5446 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7654 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0649 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1089 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.13997(4) 0.24856(4) 0.52034(3) 0.01200(9) Uani 1 1 d . . . C10 C 0.20439(15) 0.41455(14) 0.53902(13) 0.0132(3) Uani 1 1 d . . . H10A H 0.1449 0.4385 0.4867 0.016 Uiso 1 1 calc R . . H10B H 0.1890 0.4630 0.6185 0.016 Uiso 1 1 calc R . . C11 C 0.15433(16) 0.15380(14) 0.37562(13) 0.0149(3) Uani 1 1 d . . . C12 C 0.03275(17) 0.08836(15) 0.30294(14) 0.0182(3) Uani 1 1 d . . . H12 H -0.0592 0.0901 0.3310 0.022 Uiso 1 1 calc R . . C13 C 0.0464(2) 0.02045(16) 0.18911(15) 0.0248(4) Uani 1 1 d . . . H13 H -0.0362 -0.0240 0.1396 0.030 Uiso 1 1 calc R . . C14 C 0.1802(2) 0.01787(17) 0.14834(15) 0.0281(4) Uani 1 1 d . . . H14 H 0.1892 -0.0282 0.0706 0.034 Uiso 1 1 calc R . . C15 C 0.3017(2) 0.08218(16) 0.22028(15) 0.0255(4) Uani 1 1 d . . . H15 H 0.3933 0.0799 0.1917 0.031 Uiso 1 1 calc R . . C16 C 0.28920(18) 0.14969(15) 0.33382(15) 0.0202(3) Uani 1 1 d . . . H16 H 0.3723 0.1931 0.3831 0.024 Uiso 1 1 calc R . . C21 C 0.23813(15) 0.20130(14) 0.61819(13) 0.0138(3) Uani 1 1 d . . . C22 C 0.28003(16) 0.08564(15) 0.58421(14) 0.0175(3) Uani 1 1 d . . . H22 H 0.2636 0.0330 0.5065 0.021 Uiso 1 1 calc R . . C23 C 0.34635(17) 0.04820(16) 0.66550(15) 0.0216(4) Uani 1 1 d . . . H23 H 0.3746 -0.0306 0.6431 0.026 Uiso 1 1 calc R . . C24 C 0.37119(17) 0.12499(16) 0.77828(15) 0.0205(3) Uani 1 1 d . . . H24 H 0.4164 0.0988 0.8331 0.025 Uiso 1 1 calc R . . C25 C 0.33054(17) 0.24010(16) 0.81192(14) 0.0204(3) Uani 1 1 d . . . H25 H 0.3485 0.2927 0.8895 0.024 Uiso 1 1 calc R . . C26 C 0.26368(17) 0.27891(15) 0.73279(14) 0.0173(3) Uani 1 1 d . . . H26 H 0.2353 0.3576 0.7561 0.021 Uiso 1 1 calc R . . C31 C -0.04206(15) 0.23676(14) 0.55645(13) 0.0132(3) Uani 1 1 d . . . C32 C -0.08720(16) 0.20110(14) 0.65187(13) 0.0156(3) Uani 1 1 d . . . H32 H -0.0236 0.1749 0.6946 0.019 Uiso 1 1 calc R . . C33 C -0.22502(17) 0.20416(15) 0.68390(14) 0.0189(3) Uani 1 1 d . . . H33 H -0.2554 0.1812 0.7494 0.023 Uiso 1 1 calc R . . C34 C -0.31887(17) 0.24064(15) 0.62079(14) 0.0195(3) Uani 1 1 d . . . H34 H -0.4133 0.2425 0.6431 0.023 Uiso 1 1 calc R . . C35 C -0.27479(17) 0.27456(15) 0.52482(14) 0.0172(3) Uani 1 1 d . . . H35 H -0.3397 0.2982 0.4810 0.021 Uiso 1 1 calc R . . C36 C -0.13660(16) 0.27395(14) 0.49308(13) 0.0143(3) Uani 1 1 d . . . H36 H -0.1061 0.2987 0.4285 0.017 Uiso 1 1 calc R . . C41 C 0.35830(15) 0.45499(13) 0.51815(13) 0.0123(3) Uani 1 1 d . . . C42 C 0.39629(16) 0.45958(14) 0.40979(13) 0.0143(3) Uani 1 1 d . . . H42 H 0.3255 0.4319 0.3478 0.017 Uiso 1 1 calc R . . C43 C 0.46376(16) 0.49588(14) 0.60808(13) 0.0145(3) Uani 1 1 d . . . H43 H 0.4392 0.4931 0.6823 0.017 Uiso 1 1 calc R . . N1 N 0.87913(14) 0.26120(13) 0.11796(11) 0.0185(3) Uani 1 1 d . . . S1 S 0.72143(4) 0.23009(4) 0.15030(3) 0.01721(10) Uani 1 1 d . . . O11 O 0.69647(12) 0.29405(12) 0.26673(10) 0.0223(3) Uani 1 1 d . . . O12 O 0.66624(13) 0.09793(12) 0.10336(11) 0.0279(3) Uani 1 1 d . . . C1 C 0.62128(17) 0.29564(17) 0.06405(14) 0.0211(4) Uani 1 1 d . . . F11 F 0.48212(10) 0.25868(12) 0.07176(10) 0.0362(3) Uani 1 1 d . . . F12 F 0.64763(12) 0.25458(11) -0.04595(9) 0.0342(3) Uani 1 1 d . . . F13 F 0.65202(12) 0.42040(10) 0.09852(10) 0.0326(3) Uani 1 1 d . . . S2 S 0.98615(4) 0.38608(4) 0.18921(3) 0.01692(10) Uani 1 1 d . . . O21 O 1.05301(13) 0.37617(13) 0.28990(11) 0.0272(3) Uani 1 1 d . . . O22 O 0.93975(13) 0.50072(11) 0.19986(10) 0.0248(3) Uani 1 1 d . . . C2 C 1.1245(2) 0.37777(19) 0.08661(17) 0.0287(4) Uani 1 1 d . . . F21 F 1.23186(13) 0.47538(13) 0.13038(12) 0.0505(4) Uani 1 1 d . . . F22 F 1.07684(14) 0.38146(12) -0.01271(10) 0.0434(3) Uani 1 1 d . . . F23 F 1.17353(12) 0.27281(12) 0.06823(11) 0.0418(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.01103(18) 0.01277(19) 0.01213(19) 0.00417(14) 0.00154(13) 0.00191(14) C10 0.0117(7) 0.0125(7) 0.0148(7) 0.0038(6) 0.0016(5) 0.0020(6) C11 0.0187(7) 0.0134(7) 0.0132(7) 0.0049(6) 0.0035(6) 0.0035(6) C12 0.0191(8) 0.0185(8) 0.0166(8) 0.0048(6) 0.0004(6) 0.0040(6) C13 0.0352(10) 0.0213(9) 0.0159(9) 0.0027(7) -0.0028(7) 0.0066(8) C14 0.0513(12) 0.0202(9) 0.0155(8) 0.0049(7) 0.0104(8) 0.0151(9) C15 0.0342(10) 0.0201(9) 0.0270(10) 0.0101(7) 0.0179(8) 0.0116(8) C16 0.0220(8) 0.0156(8) 0.0232(9) 0.0065(6) 0.0066(7) 0.0034(7) C21 0.0108(7) 0.0151(7) 0.0153(8) 0.0061(6) 0.0005(5) 0.0005(6) C22 0.0153(7) 0.0140(8) 0.0204(8) 0.0038(6) -0.0026(6) -0.0010(6) C23 0.0186(8) 0.0140(8) 0.0321(10) 0.0081(7) -0.0048(7) 0.0021(6) C24 0.0155(8) 0.0220(9) 0.0266(9) 0.0137(7) -0.0047(6) 0.0000(7) C25 0.0192(8) 0.0261(9) 0.0171(8) 0.0086(7) 0.0005(6) 0.0047(7) C26 0.0181(8) 0.0177(8) 0.0176(8) 0.0059(6) 0.0034(6) 0.0061(6) C31 0.0126(7) 0.0117(7) 0.0139(7) 0.0033(6) 0.0021(5) 0.0001(6) C32 0.0180(7) 0.0135(8) 0.0153(8) 0.0053(6) 0.0015(6) 0.0019(6) C33 0.0207(8) 0.0178(8) 0.0181(8) 0.0071(6) 0.0070(6) 0.0016(6) C34 0.0138(7) 0.0192(8) 0.0246(9) 0.0059(7) 0.0070(6) 0.0027(6) C35 0.0155(7) 0.0151(8) 0.0206(8) 0.0050(6) 0.0006(6) 0.0033(6) C36 0.0140(7) 0.0133(7) 0.0151(8) 0.0048(6) 0.0012(6) 0.0014(6) C41 0.0124(7) 0.0097(7) 0.0149(7) 0.0037(5) 0.0022(5) 0.0025(6) C42 0.0134(7) 0.0153(8) 0.0135(7) 0.0045(6) -0.0009(5) 0.0016(6) C43 0.0155(7) 0.0152(8) 0.0125(7) 0.0044(6) 0.0025(6) 0.0025(6) N1 0.0168(6) 0.0201(7) 0.0167(7) 0.0017(5) 0.0022(5) 0.0061(6) S1 0.01867(19) 0.0195(2) 0.0142(2) 0.00516(15) 0.00226(14) 0.00582(16) O11 0.0239(6) 0.0318(7) 0.0136(6) 0.0073(5) 0.0052(5) 0.0107(5) O12 0.0300(7) 0.0193(6) 0.0318(7) 0.0060(5) 0.0049(5) 0.0020(5) C1 0.0172(8) 0.0289(10) 0.0172(8) 0.0073(7) -0.0003(6) 0.0043(7) F11 0.0165(5) 0.0583(8) 0.0397(7) 0.0249(6) 0.0002(5) 0.0059(5) F12 0.0354(6) 0.0533(8) 0.0139(5) 0.0097(5) -0.0011(4) 0.0111(6) F13 0.0352(6) 0.0290(6) 0.0374(7) 0.0133(5) -0.0082(5) 0.0110(5) S2 0.01621(19) 0.0218(2) 0.0145(2) 0.00766(15) 0.00242(14) 0.00499(16) O21 0.0226(6) 0.0392(8) 0.0215(7) 0.0162(6) -0.0045(5) 0.0000(6) O22 0.0289(7) 0.0214(6) 0.0251(7) 0.0065(5) 0.0046(5) 0.0093(5) C2 0.0269(9) 0.0345(11) 0.0333(11) 0.0197(9) 0.0139(8) 0.0113(8) F21 0.0330(7) 0.0516(9) 0.0626(9) 0.0206(7) 0.0200(6) -0.0057(6) F22 0.0595(8) 0.0620(9) 0.0259(6) 0.0277(6) 0.0211(6) 0.0301(7) F23 0.0359(7) 0.0505(8) 0.0563(8) 0.0292(6) 0.0269(6) 0.0284(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.7915(15) . ? P1 C31 1.7932(15) . ? P1 C11 1.7944(16) . ? P1 C10 1.8168(15) . ? C10 C41 1.506(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.397(2) . ? C11 C16 1.398(2) . ? C12 C13 1.394(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(3) . ? C13 H13 0.9500 . ? C14 C15 1.390(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.397(2) . ? C21 C26 1.402(2) . ? C22 C23 1.396(2) . ? C22 H22 0.9500 . ? C23 C24 1.381(2) . ? C23 H23 0.9500 . ? C24 C25 1.385(2) . ? C24 H24 0.9500 . ? C25 C26 1.387(2) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C32 1.398(2) . ? C31 C36 1.399(2) . ? C32 C33 1.385(2) . ? C32 H32 0.9500 . ? C33 C34 1.387(2) . ? C33 H33 0.9500 . ? C34 C35 1.392(2) . ? C34 H34 0.9500 . ? C35 C36 1.384(2) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.395(2) . ? C41 C43 1.395(2) . ? C42 C43 1.383(2) 2_666 ? C42 H42 0.9500 . ? C43 C42 1.383(2) 2_666 ? C43 H43 0.9500 . ? N1 S1 1.5665(14) . ? N1 S2 1.5811(14) . ? S1 O12 1.4276(13) . ? S1 O11 1.4354(12) . ? S1 C1 1.8349(17) . ? C1 F13 1.326(2) . ? C1 F12 1.3288(19) . ? C1 F11 1.3317(18) . ? S2 O22 1.4333(13) . ? S2 O21 1.4348(12) . ? S2 C2 1.8299(18) . ? C2 F22 1.316(2) . ? C2 F23 1.328(2) . ? C2 F21 1.329(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C31 109.40(7) . . ? C21 P1 C11 109.86(7) . . ? C31 P1 C11 111.71(7) . . ? C21 P1 C10 110.15(7) . . ? C31 P1 C10 104.50(7) . . ? C11 P1 C10 111.09(7) . . ? C41 C10 P1 116.96(10) . . ? C41 C10 H10A 108.1 . . ? P1 C10 H10A 108.1 . . ? C41 C10 H10B 108.1 . . ? P1 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? C12 C11 C16 119.63(15) . . ? C12 C11 P1 120.94(12) . . ? C16 C11 P1 119.38(12) . . ? C13 C12 C11 119.94(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 119.98(17) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.42(16) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C16 C15 C14 120.03(16) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 119.99(16) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C22 C21 C26 120.04(14) . . ? C22 C21 P1 121.23(12) . . ? C26 C21 P1 118.57(12) . . ? C23 C22 C21 119.32(15) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 120.40(16) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 120.33(15) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 120.29(16) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 119.62(15) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? C32 C31 C36 119.93(14) . . ? C32 C31 P1 121.07(12) . . ? C36 C31 P1 118.79(11) . . ? C33 C32 C31 119.74(14) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C32 C33 C34 120.30(14) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C35 120.08(14) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 120.17(14) . . ? C36 C35 H35 119.9 . . ? C34 C35 H35 119.9 . . ? C35 C36 C31 119.77(14) . . ? C35 C36 H36 120.1 . . ? C31 C36 H36 120.1 . . ? C42 C41 C43 118.91(13) . . ? C42 C41 C10 120.26(13) . . ? C43 C41 C10 120.70(13) . . ? C43 C42 C41 120.50(13) 2_666 . ? C43 C42 H42 119.8 2_666 . ? C41 C42 H42 119.8 . . ? C42 C43 C41 120.59(14) 2_666 . ? C42 C43 H43 119.7 2_666 . ? C41 C43 H43 119.7 . . ? S1 N1 S2 121.44(9) . . ? O12 S1 O11 119.08(8) . . ? O12 S1 N1 109.38(8) . . ? O11 S1 N1 114.94(7) . . ? O12 S1 C1 102.90(8) . . ? O11 S1 C1 104.26(8) . . ? N1 S1 C1 104.27(7) . . ? F13 C1 F12 108.25(14) . . ? F13 C1 F11 107.85(14) . . ? F12 C1 F11 107.77(13) . . ? F13 C1 S1 112.55(11) . . ? F12 C1 S1 110.74(12) . . ? F11 C1 S1 109.52(11) . . ? O22 S2 O21 117.19(8) . . ? O22 S2 N1 115.53(8) . . ? O21 S2 N1 113.33(8) . . ? O22 S2 C2 105.93(8) . . ? O21 S2 C2 104.67(8) . . ? N1 S2 C2 97.03(8) . . ? F22 C2 F23 108.28(16) . . ? F22 C2 F21 108.93(15) . . ? F23 C2 F21 108.45(16) . . ? F22 C2 S2 111.69(13) . . ? F23 C2 S2 111.09(12) . . ? F21 C2 S2 108.33(13) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C10 C41 60.72(13) . . . . ? C31 P1 C10 C41 178.13(11) . . . . ? C11 P1 C10 C41 -61.25(13) . . . . ? C21 P1 C11 C12 125.60(13) . . . . ? C31 P1 C11 C12 4.00(15) . . . . ? C10 P1 C11 C12 -112.27(13) . . . . ? C21 P1 C11 C16 -57.03(14) . . . . ? C31 P1 C11 C16 -178.63(12) . . . . ? C10 P1 C11 C16 65.11(14) . . . . ? C16 C11 C12 C13 -0.6(2) . . . . ? P1 C11 C12 C13 176.76(12) . . . . ? C11 C12 C13 C14 0.0(2) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C13 C14 C15 C16 -0.1(3) . . . . ? C14 C15 C16 C11 -0.5(2) . . . . ? C12 C11 C16 C15 0.8(2) . . . . ? P1 C11 C16 C15 -176.58(13) . . . . ? C31 P1 C21 C22 106.10(13) . . . . ? C11 P1 C21 C22 -16.87(15) . . . . ? C10 P1 C21 C22 -139.56(12) . . . . ? C31 P1 C21 C26 -69.35(13) . . . . ? C11 P1 C21 C26 167.68(12) . . . . ? C10 P1 C21 C26 44.98(14) . . . . ? C26 C21 C22 C23 0.4(2) . . . . ? P1 C21 C22 C23 -174.94(12) . . . . ? C21 C22 C23 C24 -0.4(2) . . . . ? C22 C23 C24 C25 0.0(2) . . . . ? C23 C24 C25 C26 0.4(2) . . . . ? C24 C25 C26 C21 -0.4(2) . . . . ? C22 C21 C26 C25 0.0(2) . . . . ? P1 C21 C26 C25 175.46(12) . . . . ? C21 P1 C31 C32 2.86(15) . . . . ? C11 P1 C31 C32 124.73(13) . . . . ? C10 P1 C31 C32 -115.07(13) . . . . ? C21 P1 C31 C36 177.61(12) . . . . ? C11 P1 C31 C36 -60.52(14) . . . . ? C10 P1 C31 C36 59.68(14) . . . . ? C36 C31 C32 C33 -0.7(2) . . . . ? P1 C31 C32 C33 173.97(12) . . . . ? C31 C32 C33 C34 0.9(2) . . . . ? C32 C33 C34 C35 -0.1(2) . . . . ? C33 C34 C35 C36 -1.0(2) . . . . ? C34 C35 C36 C31 1.2(2) . . . . ? C32 C31 C36 C35 -0.4(2) . . . . ? P1 C31 C36 C35 -175.19(12) . . . . ? P1 C10 C41 C42 92.27(15) . . . . ? P1 C10 C41 C43 -91.78(16) . . . . ? C43 C41 C42 C43 -0.1(2) . . . 2_666 ? C10 C41 C42 C43 175.94(14) . . . 2_666 ? C42 C41 C43 C42 0.1(2) . . . 2_666 ? C10 C41 C43 C42 -175.92(14) . . . 2_666 ? S2 N1 S1 O12 -158.62(9) . . . . ? S2 N1 S1 O11 -21.59(13) . . . . ? S2 N1 S1 C1 91.89(11) . . . . ? O12 S1 C1 F13 176.72(12) . . . . ? O11 S1 C1 F13 51.79(13) . . . . ? N1 S1 C1 F13 -69.11(13) . . . . ? O12 S1 C1 F12 -61.95(13) . . . . ? O11 S1 C1 F12 173.11(11) . . . . ? N1 S1 C1 F12 52.22(13) . . . . ? O12 S1 C1 F11 56.76(13) . . . . ? O11 S1 C1 F11 -68.17(13) . . . . ? N1 S1 C1 F11 170.93(12) . . . . ? S1 N1 S2 O22 -55.54(12) . . . . ? S1 N1 S2 O21 83.69(11) . . . . ? S1 N1 S2 C2 -166.98(10) . . . . ? O22 S2 C2 F22 -57.67(16) . . . . ? O21 S2 C2 F22 177.86(13) . . . . ? N1 S2 C2 F22 61.46(15) . . . . ? O22 S2 C2 F23 -178.68(13) . . . . ? O21 S2 C2 F23 56.86(16) . . . . ? N1 S2 C2 F23 -59.55(15) . . . . ? O22 S2 C2 F21 62.31(14) . . . . ? O21 S2 C2 F21 -62.16(14) . . . . ? N1 S2 C2 F21 -178.56(13) . . . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.428 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.071 # Attachment 'Complex_8b.cif' data_170608n1 _database_code_depnum_ccdc_archive 'CCDC 760646' #TrackingRef 'Complex_8b.cif' #============================================================================== # 6. CRYSTALLOGRAPHY _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C44 H38 P2, 2(C2 F6 N O4 S2)' _chemical_formula_sum 'C48 H38 F12 N2 O8 P2 S4' _chemical_formula_weight 1188.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 18.438(1) _cell_length_b 14.6101(8) _cell_length_c 19.745(1) _cell_angle_alpha 90.0 _cell_angle_beta 93.000(7) _cell_angle_gamma 90.0 _cell_volume 5311.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7745 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 28.9 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method ? _exptl_crystal_F_000 2424 _exptl_absorpt_coefficient_mu 0.334 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9423 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0009 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 101184 _diffrn_reflns_av_R_equivalents 0.0649 _diffrn_reflns_av_sigmaI/netI 0.0885 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.83 _reflns_number_total 12955 _reflns_number_gt 6469 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed 2.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1120P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12955 _refine_ls_number_parameters 685 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1628 _refine_ls_R_factor_gt 0.0792 _refine_ls_wR_factor_ref 0.2174 _refine_ls_wR_factor_gt 0.1899 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.30833(5) 0.35805(6) 0.17255(4) 0.0377(2) Uani 1 1 d . . . P2 P 0.68746(5) 0.47441(6) 0.16574(4) 0.0326(2) Uani 1 1 d . . . C1 C 0.33368(18) 0.4050(3) 0.09261(16) 0.0422(8) Uani 1 1 d . . . H1A H 0.3216 0.3597 0.0565 0.051 Uiso 1 1 calc R . . H1B H 0.3039 0.4602 0.0827 0.051 Uiso 1 1 calc R . . C2 C 0.63899(18) 0.5023(2) 0.08580(16) 0.0375(8) Uani 1 1 d . . . H2A H 0.6439 0.5687 0.0769 0.045 Uiso 1 1 calc R . . H2B H 0.6613 0.4688 0.0486 0.045 Uiso 1 1 calc R . . C11 C 0.34740(17) 0.2468(2) 0.18659(16) 0.0370(8) Uani 1 1 d . . . C12 C 0.3577(2) 0.1884(3) 0.13218(18) 0.0482(9) Uani 1 1 d . . . H12 H 0.3460 0.2082 0.0871 0.058 Uiso 1 1 calc R . . C13 C 0.3846(2) 0.1025(3) 0.1440(2) 0.0632(12) Uani 1 1 d . . . H13 H 0.3919 0.0626 0.1070 0.076 Uiso 1 1 calc R . . C14 C 0.4011(2) 0.0736(3) 0.2087(2) 0.0603(11) Uani 1 1 d . . . H14 H 0.4204 0.0140 0.2162 0.072 Uiso 1 1 calc R . . C15 C 0.3904(2) 0.1293(3) 0.2631(2) 0.0553(10) Uani 1 1 d . . . H15 H 0.4010 0.1080 0.3079 0.066 Uiso 1 1 calc R . . C16 C 0.3640(2) 0.2163(3) 0.25198(18) 0.0464(9) Uani 1 1 d . . . H16 H 0.3572 0.2557 0.2894 0.056 Uiso 1 1 calc R . . C21 C 0.3386(2) 0.4315(2) 0.24082(17) 0.0415(8) Uani 1 1 d . . . C22 C 0.4119(2) 0.4348(3) 0.2603(2) 0.0589(11) Uani 1 1 d . . . H22 H 0.4454 0.3972 0.2382 0.071 Uiso 1 1 calc R . . C23 C 0.4361(3) 0.4924(3) 0.3116(2) 0.0745(14) Uani 1 1 d . . . H23 H 0.4864 0.4945 0.3249 0.089 Uiso 1 1 calc R . . C24 C 0.3882(4) 0.5467(4) 0.3435(3) 0.0901(17) Uani 1 1 d . . . H24 H 0.4051 0.5862 0.3791 0.108 Uiso 1 1 calc R . . C25 C 0.3148(3) 0.5444(4) 0.3240(3) 0.0968(18) Uani 1 1 d . . . H25 H 0.2817 0.5827 0.3460 0.116 Uiso 1 1 calc R . . C26 C 0.2899(3) 0.4867(3) 0.2729(2) 0.0671(12) Uani 1 1 d . . . H26 H 0.2396 0.4848 0.2597 0.080 Uiso 1 1 calc R . . C31 C 0.21095(19) 0.3478(2) 0.16922(18) 0.0412(8) Uani 1 1 d . . . C32 C 0.1671(2) 0.3923(3) 0.1205(2) 0.0631(11) Uani 1 1 d . . . H32 H 0.1886 0.4307 0.0883 0.076 Uiso 1 1 calc R . . C33 C 0.0936(2) 0.3817(4) 0.1183(3) 0.0744(13) Uani 1 1 d . . . H33 H 0.0642 0.4133 0.0850 0.089 Uiso 1 1 calc R . . C34 C 0.0625(3) 0.3268(4) 0.1628(3) 0.0824(15) Uani 1 1 d . . . H34 H 0.0114 0.3178 0.1597 0.099 Uiso 1 1 calc R . . C35 C 0.1044(3) 0.2836(4) 0.2129(3) 0.0917(17) Uani 1 1 d . . . H35 H 0.0821 0.2472 0.2458 0.110 Uiso 1 1 calc R . . C36 C 0.1790(2) 0.2932(3) 0.2152(3) 0.0709(13) Uani 1 1 d . . . H36 H 0.2081 0.2618 0.2488 0.085 Uiso 1 1 calc R . . C41 C 0.65971(18) 0.5498(2) 0.23176(16) 0.0385(8) Uani 1 1 d . . . C42 C 0.6401(2) 0.6384(3) 0.2156(2) 0.0524(10) Uani 1 1 d . . . H42 H 0.6396 0.6583 0.1698 0.063 Uiso 1 1 calc R . . C43 C 0.6211(3) 0.6982(3) 0.2656(2) 0.0675(12) Uani 1 1 d . . . H43 H 0.6073 0.7593 0.2547 0.081 Uiso 1 1 calc R . . C44 C 0.6226(3) 0.6681(4) 0.3319(3) 0.0751(14) Uani 1 1 d . . . H44 H 0.6085 0.7088 0.3664 0.090 Uiso 1 1 calc R . . C45 C 0.6434(3) 0.5820(4) 0.3491(2) 0.0776(14) Uani 1 1 d . . . H45 H 0.6444 0.5628 0.3951 0.093 Uiso 1 1 calc R . . C46 C 0.6634(2) 0.5218(3) 0.29856(19) 0.0573(10) Uani 1 1 d . . . H46 H 0.6796 0.4618 0.3101 0.069 Uiso 1 1 calc R . . C51 C 0.78325(18) 0.4867(2) 0.15725(17) 0.0367(8) Uani 1 1 d . . . C52 C 0.8110(2) 0.5308(3) 0.1022(2) 0.0581(11) Uani 1 1 d . . . H52 H 0.7793 0.5519 0.0661 0.070 Uiso 1 1 calc R . . C53 C 0.8843(2) 0.5438(3) 0.1000(3) 0.0691(12) Uani 1 1 d . . . H53 H 0.9033 0.5746 0.0625 0.083 Uiso 1 1 calc R . . C54 C 0.9302(2) 0.5132(3) 0.1512(3) 0.0652(12) Uani 1 1 d . . . H54 H 0.9810 0.5229 0.1492 0.078 Uiso 1 1 calc R . . C55 C 0.9040(2) 0.4687(3) 0.2050(2) 0.0615(11) Uani 1 1 d . . . H55 H 0.9364 0.4472 0.2404 0.074 Uiso 1 1 calc R . . C56 C 0.83027(19) 0.4546(3) 0.20831(19) 0.0472(9) Uani 1 1 d . . . H56 H 0.8120 0.4229 0.2458 0.057 Uiso 1 1 calc R . . C61 C 0.66534(18) 0.3589(2) 0.18488(17) 0.0378(8) Uani 1 1 d . . . C62 C 0.6065(2) 0.3380(3) 0.2221(2) 0.0597(11) Uani 1 1 d . . . H62 H 0.5810 0.3854 0.2436 0.072 Uiso 1 1 calc R . . C63 C 0.5846(3) 0.2477(3) 0.2284(3) 0.0823(15) Uani 1 1 d . . . H63 H 0.5442 0.2331 0.2543 0.099 Uiso 1 1 calc R . . C64 C 0.6209(3) 0.1809(3) 0.1974(3) 0.0859(16) Uani 1 1 d . . . H64 H 0.6058 0.1190 0.2015 0.103 Uiso 1 1 calc R . . C65 C 0.6784(3) 0.2011(3) 0.1609(3) 0.0806(15) Uani 1 1 d . . . H65 H 0.7030 0.1530 0.1393 0.097 Uiso 1 1 calc R . . C66 C 0.7025(2) 0.2888(2) 0.1541(2) 0.0538(10) Uani 1 1 d . . . H66 H 0.7437 0.3017 0.1288 0.065 Uiso 1 1 calc R . . C71 C 0.41290(18) 0.4307(2) 0.08948(15) 0.0365(8) Uani 1 1 d . . . C72 C 0.4636(2) 0.3691(3) 0.06797(17) 0.0443(9) Uani 1 1 d . . . H72 H 0.4486 0.3096 0.0539 0.053 Uiso 1 1 calc R . . C73 C 0.53600(19) 0.3931(2) 0.06663(17) 0.0430(8) Uani 1 1 d . . . H73 H 0.5700 0.3496 0.0518 0.052 Uiso 1 1 calc R . . C74 C 0.55961(18) 0.4781(2) 0.08619(15) 0.0344(7) Uani 1 1 d . . . C75 C 0.50825(19) 0.5411(2) 0.10605(17) 0.0419(8) Uani 1 1 d . . . H75 H 0.5230 0.6015 0.1182 0.050 Uiso 1 1 calc R . . C76 C 0.43691(19) 0.5170(2) 0.10829(19) 0.0459(9) Uani 1 1 d . . . H76 H 0.4030 0.5607 0.1231 0.055 Uiso 1 1 calc R . . S1A S 0.25388(7) 0.17119(8) 0.42266(6) 0.0669(3) Uani 1 1 d . . . S2A S 0.39653(7) 0.17892(8) 0.47644(5) 0.0668(3) Uani 1 1 d . . . O11A O 0.2233(2) 0.1524(3) 0.35619(17) 0.1005(12) Uani 1 1 d . . . O12A O 0.2349(2) 0.1126(2) 0.47554(17) 0.0891(10) Uani 1 1 d . . . O21A O 0.3729(2) 0.1837(2) 0.54321(14) 0.0819(10) Uani 1 1 d . . . O22A O 0.4452(3) 0.1090(3) 0.4602(2) 0.1289(16) Uani 1 1 d . . . N1A N 0.3354(2) 0.1900(3) 0.41738(16) 0.0729(11) Uani 1 1 d . . . C1A C 0.2150(4) 0.2826(5) 0.4438(4) 0.1046(19) Uani 1 1 d . . . C2A C 0.4452(3) 0.2854(6) 0.4643(3) 0.0958(19) Uani 1 1 d . . . F11A F 0.1443(3) 0.2721(4) 0.4482(3) 0.185(2) Uani 1 1 d . . . F12A F 0.2435(3) 0.3123(3) 0.5029(2) 0.1381(14) Uani 1 1 d . . . F13A F 0.2272(3) 0.3427(3) 0.3974(2) 0.1628(19) Uani 1 1 d . . . F21A F 0.4991(2) 0.2914(4) 0.5091(2) 0.1583(17) Uani 1 1 d . . . F22A F 0.4712(2) 0.2886(3) 0.40363(19) 0.1480(16) Uani 1 1 d . . . F23A F 0.4030(3) 0.3562(3) 0.4721(2) 0.1392(15) Uani 1 1 d . . . S1B S 0.86854(12) 0.44315(11) 0.43507(8) 0.1133(7) Uani 1 1 d . . . S2B S 0.77236(7) 0.29681(8) 0.42693(6) 0.0674(3) Uani 1 1 d . . . O11B O 0.8437(3) 0.4744(3) 0.3719(2) 0.157(2) Uani 1 1 d . . . O12B O 0.8865(4) 0.5082(3) 0.4854(2) 0.163(2) Uani 1 1 d . . . O21B O 0.7601(2) 0.3109(3) 0.35648(16) 0.0938(11) Uani 1 1 d . . . O22B O 0.7880(2) 0.2081(2) 0.45112(19) 0.0983(11) Uani 1 1 d . . . N1B N 0.8227(3) 0.3647(3) 0.46666(19) 0.0999(16) Uani 1 1 d . . . C1B C 0.9533(5) 0.3852(6) 0.4232(4) 0.126(2) Uani 1 1 d . . . C2B C 0.6880(4) 0.3255(6) 0.4628(4) 0.119(2) Uani 1 1 d . . . F11B F 1.0005(3) 0.4395(5) 0.3985(3) 0.241(3) Uani 1 1 d . . . F12B F 0.9838(2) 0.3582(3) 0.4821(3) 0.1602(17) Uani 1 1 d . . . F13B F 0.9411(3) 0.3154(4) 0.3812(3) 0.210(3) Uani 1 1 d . . . F21B F 0.6361(3) 0.2654(5) 0.4358(3) 0.211(3) Uani 1 1 d . . . F22B F 0.6891(3) 0.3097(3) 0.5285(2) 0.1534(17) Uani 1 1 d . . . F23B F 0.6620(3) 0.3996(4) 0.4505(3) 0.198(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0296(5) 0.0435(5) 0.0399(5) 0.0016(4) 0.0012(4) 0.0032(4) P2 0.0303(5) 0.0315(4) 0.0361(5) 0.0010(4) 0.0037(4) 0.0015(4) C1 0.0349(19) 0.052(2) 0.0394(19) 0.0114(16) -0.0032(15) -0.0005(17) C2 0.0338(19) 0.046(2) 0.0332(17) 0.0024(15) 0.0034(14) -0.0003(15) C11 0.0278(17) 0.045(2) 0.0384(19) 0.0024(15) 0.0034(14) 0.0049(15) C12 0.056(2) 0.051(2) 0.037(2) -0.0032(17) -0.0029(17) 0.0067(19) C13 0.079(3) 0.056(3) 0.055(3) -0.013(2) 0.010(2) 0.007(2) C14 0.063(3) 0.050(2) 0.069(3) 0.004(2) 0.007(2) 0.016(2) C15 0.059(3) 0.063(3) 0.044(2) 0.0090(19) 0.0052(19) 0.016(2) C16 0.047(2) 0.052(2) 0.041(2) -0.0009(17) 0.0070(17) 0.0110(18) C21 0.042(2) 0.042(2) 0.0409(19) -0.0008(16) 0.0021(16) 0.0020(17) C22 0.049(2) 0.068(3) 0.058(2) -0.011(2) -0.003(2) 0.006(2) C23 0.063(3) 0.079(3) 0.080(3) -0.022(3) -0.016(3) -0.010(3) C24 0.108(5) 0.072(3) 0.087(4) -0.034(3) -0.020(3) -0.008(3) C25 0.097(4) 0.080(4) 0.114(4) -0.051(3) 0.013(4) 0.016(3) C26 0.059(3) 0.060(3) 0.082(3) -0.021(2) 0.003(2) 0.008(2) C31 0.0334(19) 0.042(2) 0.049(2) -0.0034(16) 0.0050(16) 0.0006(16) C32 0.037(2) 0.080(3) 0.072(3) 0.005(2) 0.002(2) 0.005(2) C33 0.036(2) 0.096(4) 0.090(3) 0.003(3) -0.007(2) 0.012(2) C34 0.036(2) 0.074(3) 0.137(5) -0.008(3) 0.000(3) -0.001(2) C35 0.058(3) 0.073(3) 0.148(5) 0.025(3) 0.041(3) -0.010(3) C36 0.043(2) 0.066(3) 0.105(4) 0.026(3) 0.016(2) 0.004(2) C41 0.0355(19) 0.042(2) 0.0383(19) -0.0065(15) 0.0021(15) -0.0006(15) C42 0.059(3) 0.042(2) 0.056(2) -0.0115(18) 0.0043(19) 0.0019(19) C43 0.072(3) 0.048(2) 0.081(3) -0.023(2) -0.003(2) 0.009(2) C44 0.067(3) 0.084(4) 0.075(3) -0.048(3) 0.008(3) 0.003(3) C45 0.092(4) 0.094(4) 0.048(3) -0.018(3) 0.010(2) 0.005(3) C46 0.065(3) 0.062(3) 0.046(2) -0.007(2) 0.0044(19) 0.005(2) C51 0.0321(18) 0.0314(17) 0.047(2) -0.0051(15) 0.0053(15) -0.0012(15) C52 0.040(2) 0.070(3) 0.065(3) 0.017(2) 0.0069(19) -0.005(2) C53 0.049(3) 0.072(3) 0.088(3) 0.013(2) 0.021(3) -0.007(2) C54 0.029(2) 0.070(3) 0.097(4) -0.016(3) 0.007(2) -0.008(2) C55 0.034(2) 0.071(3) 0.078(3) -0.009(2) -0.009(2) 0.004(2) C56 0.033(2) 0.056(2) 0.052(2) -0.0026(18) -0.0020(17) -0.0010(17) C61 0.0374(19) 0.0318(18) 0.0437(19) 0.0042(15) -0.0024(15) 0.0025(15) C62 0.053(3) 0.049(2) 0.079(3) 0.004(2) 0.023(2) -0.006(2) C63 0.076(3) 0.066(3) 0.109(4) 0.024(3) 0.036(3) -0.010(3) C64 0.093(4) 0.038(3) 0.128(4) 0.018(3) 0.022(4) -0.013(3) C65 0.077(4) 0.035(2) 0.131(4) -0.004(3) 0.015(3) 0.010(2) C66 0.049(2) 0.041(2) 0.072(3) 0.0016(19) 0.012(2) 0.0030(19) C71 0.0333(19) 0.044(2) 0.0314(17) 0.0094(15) -0.0037(14) 0.0005(16) C72 0.045(2) 0.046(2) 0.042(2) -0.0082(16) 0.0046(17) -0.0045(18) C73 0.038(2) 0.047(2) 0.045(2) -0.0091(17) 0.0072(16) 0.0028(17) C74 0.0349(18) 0.0429(19) 0.0251(16) 0.0034(14) -0.0004(13) 0.0002(16) C75 0.041(2) 0.0340(18) 0.051(2) 0.0020(15) 0.0000(17) 0.0028(16) C76 0.034(2) 0.044(2) 0.060(2) 0.0048(18) -0.0001(17) 0.0102(17) S1A 0.0675(8) 0.0727(8) 0.0617(7) 0.0029(6) 0.0138(6) -0.0272(6) S2A 0.0762(8) 0.0758(8) 0.0489(6) -0.0096(5) 0.0088(6) 0.0001(6) O11A 0.097(3) 0.130(3) 0.075(2) -0.006(2) 0.0034(19) -0.052(2) O12A 0.095(3) 0.088(2) 0.085(2) 0.0202(18) 0.0126(19) -0.031(2) O21A 0.120(3) 0.081(2) 0.0448(17) -0.0065(15) 0.0065(17) -0.014(2) O22A 0.146(4) 0.128(3) 0.115(3) -0.020(3) 0.028(3) 0.057(3) N1A 0.073(3) 0.102(3) 0.0449(19) -0.0089(19) 0.0162(18) -0.031(2) C1A 0.089(5) 0.100(5) 0.126(6) 0.006(4) 0.019(4) 0.002(4) C2A 0.067(4) 0.150(6) 0.070(4) 0.017(4) -0.002(3) -0.030(4) F11A 0.100(3) 0.181(4) 0.278(6) 0.037(4) 0.042(4) 0.050(3) F12A 0.164(4) 0.122(3) 0.130(3) -0.033(2) 0.027(3) 0.032(3) F13A 0.237(6) 0.093(3) 0.158(4) 0.054(3) 0.004(3) 0.018(3) F21A 0.114(3) 0.232(5) 0.124(3) 0.025(3) -0.039(2) -0.082(3) F22A 0.100(3) 0.240(5) 0.105(3) 0.043(3) 0.009(2) -0.068(3) F23A 0.158(4) 0.089(3) 0.170(4) 0.007(2) 0.013(3) -0.042(3) S1B 0.1727(19) 0.0846(10) 0.0791(10) 0.0192(8) -0.0261(10) -0.0465(11) S2B 0.0727(8) 0.0580(7) 0.0705(8) 0.0023(6) -0.0061(6) 0.0054(6) O11B 0.243(6) 0.126(4) 0.095(3) 0.055(3) -0.055(3) -0.053(4) O12B 0.268(7) 0.091(3) 0.123(3) -0.023(3) -0.055(4) -0.062(4) O21B 0.112(3) 0.106(3) 0.061(2) -0.0062(18) -0.0206(19) 0.006(2) O22B 0.119(3) 0.056(2) 0.120(3) 0.0165(19) 0.000(2) 0.009(2) N1B 0.134(4) 0.110(3) 0.054(2) 0.009(2) -0.009(2) -0.059(3) C1B 0.120(6) 0.143(7) 0.114(6) 0.026(5) -0.003(5) -0.041(6) C2B 0.109(6) 0.122(6) 0.127(6) 0.016(5) 0.027(5) 0.022(5) F11B 0.223(6) 0.336(8) 0.166(4) 0.006(5) 0.034(4) -0.195(6) F12B 0.118(3) 0.182(4) 0.177(4) 0.030(3) -0.029(3) -0.032(3) F13B 0.179(5) 0.216(6) 0.234(6) -0.083(5) -0.009(4) -0.072(4) F21B 0.098(3) 0.264(7) 0.271(7) -0.052(5) 0.011(4) -0.008(4) F22B 0.161(4) 0.182(4) 0.123(3) 0.033(3) 0.067(3) 0.026(3) F23B 0.216(6) 0.181(5) 0.205(5) 0.073(4) 0.094(4) 0.131(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C21 1.789(4) . ? P1 C11 1.793(3) . ? P1 C31 1.799(4) . ? P1 C1 1.805(3) . ? P2 C61 1.781(3) . ? P2 C51 1.792(3) . ? P2 C41 1.801(3) . ? P2 C2 1.819(3) . ? C1 C71 1.512(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C74 1.506(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 C16 1.385(5) . ? C11 C12 1.393(5) . ? C12 C13 1.366(5) . ? C12 H12 0.9500 . ? C13 C14 1.365(6) . ? C13 H13 0.9500 . ? C14 C15 1.369(5) . ? C14 H14 0.9500 . ? C15 C16 1.374(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C26 1.384(5) . ? C21 C22 1.388(5) . ? C22 C23 1.373(6) . ? C22 H22 0.9500 . ? C23 C24 1.366(7) . ? C23 H23 0.9500 . ? C24 C25 1.389(8) . ? C24 H24 0.9500 . ? C25 C26 1.375(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.365(5) . ? C31 C32 1.386(5) . ? C32 C33 1.364(6) . ? C32 H32 0.9500 . ? C33 C34 1.340(7) . ? C33 H33 0.9500 . ? C34 C35 1.377(7) . ? C34 H34 0.9500 . ? C35 C36 1.380(6) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.377(5) . ? C41 C46 1.379(5) . ? C42 C43 1.378(5) . ? C42 H42 0.9500 . ? C43 C44 1.380(6) . ? C43 H43 0.9500 . ? C44 C45 1.353(7) . ? C44 H44 0.9500 . ? C45 C46 1.394(6) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C51 C56 1.377(5) . ? C51 C52 1.384(5) . ? C52 C53 1.367(6) . ? C52 H52 0.9500 . ? C53 C54 1.359(6) . ? C53 H53 0.9500 . ? C54 C55 1.356(6) . ? C54 H54 0.9500 . ? C55 C56 1.379(5) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C61 C62 1.376(5) . ? C61 C66 1.390(5) . ? C62 C63 1.387(6) . ? C62 H62 0.9500 . ? C63 C64 1.348(7) . ? C63 H63 0.9500 . ? C64 C65 1.347(7) . ? C64 H64 0.9500 . ? C65 C66 1.364(6) . ? C65 H65 0.9500 . ? C66 H66 0.9500 . ? C71 C72 1.381(5) . ? C71 C76 1.381(5) . ? C72 C73 1.382(5) . ? C72 H72 0.9500 . ? C73 C74 1.365(5) . ? C73 H73 0.9500 . ? C74 C75 1.391(5) . ? C75 C76 1.364(5) . ? C75 H75 0.9500 . ? C76 H76 0.9500 . ? S1A O12A 1.408(3) . ? S1A O11A 1.428(3) . ? S1A N1A 1.537(4) . ? S1A C1A 1.835(7) . ? S2A O22A 1.407(4) . ? S2A O21A 1.412(3) . ? S2A N1A 1.587(4) . ? S2A C2A 1.818(7) . ? C1A F13A 1.297(7) . ? C1A F11A 1.319(7) . ? C1A F12A 1.328(7) . ? C2A F21A 1.299(6) . ? C2A F23A 1.309(8) . ? C2A F22A 1.314(6) . ? S1B O11B 1.384(4) . ? S1B O12B 1.403(4) . ? S1B N1B 1.573(4) . ? S1B C1B 1.804(9) . ? S2B O22B 1.406(3) . ? S2B O21B 1.413(3) . ? S2B N1B 1.544(4) . ? S2B C2B 1.791(8) . ? C1B F11B 1.292(7) . ? C1B F12B 1.324(8) . ? C1B F13B 1.327(9) . ? C2B F23B 1.204(7) . ? C2B F22B 1.318(8) . ? C2B F21B 1.385(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C21 P1 C11 108.69(16) . . ? C21 P1 C31 110.38(16) . . ? C11 P1 C31 108.80(16) . . ? C21 P1 C1 110.25(17) . . ? C11 P1 C1 111.07(16) . . ? C31 P1 C1 107.64(16) . . ? C61 P2 C51 110.64(16) . . ? C61 P2 C41 110.40(16) . . ? C51 P2 C41 108.98(15) . . ? C61 P2 C2 106.80(16) . . ? C51 P2 C2 109.77(15) . . ? C41 P2 C2 110.23(16) . . ? C71 C1 P1 115.1(2) . . ? C71 C1 H1A 108.5 . . ? P1 C1 H1A 108.5 . . ? C71 C1 H1B 108.5 . . ? P1 C1 H1B 108.5 . . ? H1A C1 H1B 107.5 . . ? C74 C2 P2 112.1(2) . . ? C74 C2 H2A 109.2 . . ? P2 C2 H2A 109.2 . . ? C74 C2 H2B 109.2 . . ? P2 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C16 C11 C12 119.3(3) . . ? C16 C11 P1 120.2(3) . . ? C12 C11 P1 120.4(3) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.3(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.1(4) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 119.3(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C11 120.4(3) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C26 C21 C22 119.9(4) . . ? C26 C21 P1 120.7(3) . . ? C22 C21 P1 119.4(3) . . ? C23 C22 C21 120.0(4) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C22 120.2(5) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C23 C24 C25 120.2(4) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 120.1(5) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? C25 C26 C21 119.6(4) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? C36 C31 C32 118.6(4) . . ? C36 C31 P1 119.3(3) . . ? C32 C31 P1 122.1(3) . . ? C33 C32 C31 120.8(4) . . ? C33 C32 H32 119.6 . . ? C31 C32 H32 119.6 . . ? C34 C33 C32 120.4(5) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 120.2(4) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C34 C35 C36 119.8(5) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C31 C36 C35 120.1(5) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C42 C41 C46 119.9(3) . . ? C42 C41 P2 119.2(3) . . ? C46 C41 P2 120.6(3) . . ? C41 C42 C43 120.3(4) . . ? C41 C42 H42 119.9 . . ? C43 C42 H42 119.9 . . ? C42 C43 C44 119.0(4) . . ? C42 C43 H43 120.5 . . ? C44 C43 H43 120.5 . . ? C45 C44 C43 121.6(4) . . ? C45 C44 H44 119.2 . . ? C43 C44 H44 119.2 . . ? C44 C45 C46 119.4(4) . . ? C44 C45 H45 120.3 . . ? C46 C45 H45 120.3 . . ? C41 C46 C45 119.7(4) . . ? C41 C46 H46 120.1 . . ? C45 C46 H46 120.1 . . ? C56 C51 C52 119.3(3) . . ? C56 C51 P2 118.9(3) . . ? C52 C51 P2 121.8(3) . . ? C53 C52 C51 119.7(4) . . ? C53 C52 H52 120.1 . . ? C51 C52 H52 120.1 . . ? C54 C53 C52 120.6(4) . . ? C54 C53 H53 119.7 . . ? C52 C53 H53 119.7 . . ? C55 C54 C53 120.4(4) . . ? C55 C54 H54 119.8 . . ? C53 C54 H54 119.8 . . ? C54 C55 C56 120.1(4) . . ? C54 C55 H55 119.9 . . ? C56 C55 H55 119.9 . . ? C51 C56 C55 119.9(4) . . ? C51 C56 H56 120.1 . . ? C55 C56 H56 120.1 . . ? C62 C61 C66 119.3(3) . . ? C62 C61 P2 121.3(3) . . ? C66 C61 P2 118.8(3) . . ? C61 C62 C63 120.1(4) . . ? C61 C62 H62 120.0 . . ? C63 C62 H62 120.0 . . ? C64 C63 C62 119.6(4) . . ? C64 C63 H63 120.2 . . ? C62 C63 H63 120.2 . . ? C65 C64 C63 120.5(4) . . ? C65 C64 H64 119.8 . . ? C63 C64 H64 119.8 . . ? C64 C65 C66 121.9(4) . . ? C64 C65 H65 119.0 . . ? C66 C65 H65 119.0 . . ? C65 C66 C61 118.6(4) . . ? C65 C66 H66 120.7 . . ? C61 C66 H66 120.7 . . ? C72 C71 C76 117.7(3) . . ? C72 C71 C1 121.5(3) . . ? C76 C71 C1 120.8(3) . . ? C71 C72 C73 120.7(3) . . ? C71 C72 H72 119.6 . . ? C73 C72 H72 119.6 . . ? C74 C73 C72 121.3(3) . . ? C74 C73 H73 119.3 . . ? C72 C73 H73 119.3 . . ? C73 C74 C75 118.0(3) . . ? C73 C74 C2 120.5(3) . . ? C75 C74 C2 121.5(3) . . ? C76 C75 C74 120.7(3) . . ? C76 C75 H75 119.7 . . ? C74 C75 H75 119.7 . . ? C75 C76 C71 121.5(3) . . ? C75 C76 H76 119.3 . . ? C71 C76 H76 119.3 . . ? O12A S1A O11A 117.6(2) . . ? O12A S1A N1A 116.1(2) . . ? O11A S1A N1A 108.2(2) . . ? O12A S1A C1A 104.8(3) . . ? O11A S1A C1A 103.9(3) . . ? N1A S1A C1A 104.6(3) . . ? O22A S2A O21A 118.7(2) . . ? O22A S2A N1A 110.1(2) . . ? O21A S2A N1A 116.0(2) . . ? O22A S2A C2A 105.4(3) . . ? O21A S2A C2A 105.1(3) . . ? N1A S2A C2A 98.8(2) . . ? S1A N1A S2A 126.3(2) . . ? F13A C1A F11A 109.5(7) . . ? F13A C1A F12A 108.8(6) . . ? F11A C1A F12A 109.0(6) . . ? F13A C1A S1A 110.9(5) . . ? F11A C1A S1A 108.2(5) . . ? F12A C1A S1A 110.4(5) . . ? F21A C2A F23A 107.7(6) . . ? F21A C2A F22A 108.5(5) . . ? F23A C2A F22A 109.0(6) . . ? F21A C2A S2A 109.5(5) . . ? F23A C2A S2A 111.1(4) . . ? F22A C2A S2A 110.9(5) . . ? O11B S1B O12B 118.0(3) . . ? O11B S1B N1B 116.0(3) . . ? O12B S1B N1B 109.0(3) . . ? O11B S1B C1B 106.7(4) . . ? O12B S1B C1B 103.7(4) . . ? N1B S1B C1B 101.3(3) . . ? O22B S2B O21B 119.2(2) . . ? O22B S2B N1B 108.2(3) . . ? O21B S2B N1B 117.9(2) . . ? O22B S2B C2B 104.4(3) . . ? O21B S2B C2B 104.9(3) . . ? N1B S2B C2B 99.2(4) . . ? S2B N1B S1B 126.0(3) . . ? F11B C1B F12B 104.6(7) . . ? F11B C1B F13B 109.3(7) . . ? F12B C1B F13B 111.7(7) . . ? F11B C1B S1B 111.5(7) . . ? F12B C1B S1B 110.9(6) . . ? F13B C1B S1B 108.8(6) . . ? F23B C2B F22B 109.9(7) . . ? F23B C2B F21B 103.4(8) . . ? F22B C2B F21B 104.0(7) . . ? F23B C2B S2B 118.5(6) . . ? F22B C2B S2B 112.4(6) . . ? F21B C2B S2B 107.3(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C21 P1 C1 C71 51.5(3) . . . . ? C11 P1 C1 C71 -69.0(3) . . . . ? C31 P1 C1 C71 172.0(3) . . . . ? C61 P2 C2 C74 50.4(3) . . . . ? C51 P2 C2 C74 170.4(2) . . . . ? C41 P2 C2 C74 -69.6(3) . . . . ? C21 P1 C11 C16 29.1(3) . . . . ? C31 P1 C11 C16 -91.2(3) . . . . ? C1 P1 C11 C16 150.5(3) . . . . ? C21 P1 C11 C12 -154.4(3) . . . . ? C31 P1 C11 C12 85.3(3) . . . . ? C1 P1 C11 C12 -33.0(3) . . . . ? C16 C11 C12 C13 -0.7(5) . . . . ? P1 C11 C12 C13 -177.2(3) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? C12 C13 C14 C15 0.8(7) . . . . ? C13 C14 C15 C16 -1.5(7) . . . . ? C14 C15 C16 C11 1.0(6) . . . . ? C12 C11 C16 C15 0.0(5) . . . . ? P1 C11 C16 C15 176.6(3) . . . . ? C11 P1 C21 C26 -133.3(3) . . . . ? C31 P1 C21 C26 -14.0(4) . . . . ? C1 P1 C21 C26 104.8(3) . . . . ? C11 P1 C21 C22 48.6(3) . . . . ? C31 P1 C21 C22 167.8(3) . . . . ? C1 P1 C21 C22 -73.4(3) . . . . ? C26 C21 C22 C23 0.4(6) . . . . ? P1 C21 C22 C23 178.5(3) . . . . ? C21 C22 C23 C24 -0.1(7) . . . . ? C22 C23 C24 C25 -0.4(8) . . . . ? C23 C24 C25 C26 0.6(9) . . . . ? C24 C25 C26 C21 -0.4(8) . . . . ? C22 C21 C26 C25 -0.1(7) . . . . ? P1 C21 C26 C25 -178.3(4) . . . . ? C21 P1 C31 C36 -76.4(3) . . . . ? C11 P1 C31 C36 42.8(4) . . . . ? C1 P1 C31 C36 163.2(3) . . . . ? C21 P1 C31 C32 104.9(3) . . . . ? C11 P1 C31 C32 -136.0(3) . . . . ? C1 P1 C31 C32 -15.5(4) . . . . ? C36 C31 C32 C33 -0.2(6) . . . . ? P1 C31 C32 C33 178.5(3) . . . . ? C31 C32 C33 C34 -0.9(7) . . . . ? C32 C33 C34 C35 2.6(8) . . . . ? C33 C34 C35 C36 -3.2(8) . . . . ? C32 C31 C36 C35 -0.4(6) . . . . ? P1 C31 C36 C35 -179.2(4) . . . . ? C34 C35 C36 C31 2.1(8) . . . . ? C61 P2 C41 C42 -150.1(3) . . . . ? C51 P2 C41 C42 88.2(3) . . . . ? C2 P2 C41 C42 -32.3(3) . . . . ? C61 P2 C41 C46 35.0(4) . . . . ? C51 P2 C41 C46 -86.7(3) . . . . ? C2 P2 C41 C46 152.8(3) . . . . ? C46 C41 C42 C43 -2.7(6) . . . . ? P2 C41 C42 C43 -177.7(3) . . . . ? C41 C42 C43 C44 0.3(6) . . . . ? C42 C43 C44 C45 1.3(7) . . . . ? C43 C44 C45 C46 -0.5(8) . . . . ? C42 C41 C46 C45 3.5(6) . . . . ? P2 C41 C46 C45 178.4(3) . . . . ? C44 C45 C46 C41 -1.9(7) . . . . ? C61 P2 C51 C56 -51.9(3) . . . . ? C41 P2 C51 C56 69.7(3) . . . . ? C2 P2 C51 C56 -169.5(3) . . . . ? C61 P2 C51 C52 130.8(3) . . . . ? C41 P2 C51 C52 -107.6(3) . . . . ? C2 P2 C51 C52 13.2(3) . . . . ? C56 C51 C52 C53 -1.5(6) . . . . ? P2 C51 C52 C53 175.7(3) . . . . ? C51 C52 C53 C54 0.6(7) . . . . ? C52 C53 C54 C55 0.4(7) . . . . ? C53 C54 C55 C56 -0.3(7) . . . . ? C52 C51 C56 C55 1.6(5) . . . . ? P2 C51 C56 C55 -175.7(3) . . . . ? C54 C55 C56 C51 -0.7(6) . . . . ? C51 P2 C61 C62 150.7(3) . . . . ? C41 P2 C61 C62 29.9(4) . . . . ? C2 P2 C61 C62 -89.9(3) . . . . ? C51 P2 C61 C66 -37.9(3) . . . . ? C41 P2 C61 C66 -158.6(3) . . . . ? C2 P2 C61 C66 81.6(3) . . . . ? C66 C61 C62 C63 -0.3(6) . . . . ? P2 C61 C62 C63 171.1(4) . . . . ? C61 C62 C63 C64 -0.4(8) . . . . ? C62 C63 C64 C65 0.3(9) . . . . ? C63 C64 C65 C66 0.5(9) . . . . ? C64 C65 C66 C61 -1.2(7) . . . . ? C62 C61 C66 C65 1.1(6) . . . . ? P2 C61 C66 C65 -170.5(3) . . . . ? P1 C1 C71 C72 90.7(4) . . . . ? P1 C1 C71 C76 -89.2(4) . . . . ? C76 C71 C72 C73 1.1(5) . . . . ? C1 C71 C72 C73 -178.8(3) . . . . ? C71 C72 C73 C74 -0.2(5) . . . . ? C72 C73 C74 C75 -1.6(5) . . . . ? C72 C73 C74 C2 178.7(3) . . . . ? P2 C2 C74 C73 -89.0(3) . . . . ? P2 C2 C74 C75 91.3(3) . . . . ? C73 C74 C75 C76 2.5(5) . . . . ? C2 C74 C75 C76 -177.8(3) . . . . ? C74 C75 C76 C71 -1.6(5) . . . . ? C72 C71 C76 C75 -0.2(5) . . . . ? C1 C71 C76 C75 179.7(3) . . . . ? O12A S1A N1A S2A -21.7(4) . . . . ? O11A S1A N1A S2A -156.4(3) . . . . ? C1A S1A N1A S2A 93.3(4) . . . . ? O22A S2A N1A S1A 115.0(4) . . . . ? O21A S2A N1A S1A -23.3(4) . . . . ? C2A S2A N1A S1A -134.9(4) . . . . ? O12A S1A C1A F13A -178.3(5) . . . . ? O11A S1A C1A F13A -54.3(6) . . . . ? N1A S1A C1A F13A 59.0(6) . . . . ? O12A S1A C1A F11A -58.2(6) . . . . ? O11A S1A C1A F11A 65.8(6) . . . . ? N1A S1A C1A F11A 179.1(5) . . . . ? O12A S1A C1A F12A 61.0(5) . . . . ? O11A S1A C1A F12A -175.0(4) . . . . ? N1A S1A C1A F12A -61.7(5) . . . . ? O22A S2A C2A F21A -66.8(6) . . . . ? O21A S2A C2A F21A 59.4(6) . . . . ? N1A S2A C2A F21A 179.5(5) . . . . ? O22A S2A C2A F23A 174.4(4) . . . . ? O21A S2A C2A F23A -59.5(5) . . . . ? N1A S2A C2A F23A 60.6(5) . . . . ? O22A S2A C2A F22A 52.9(5) . . . . ? O21A S2A C2A F22A 179.1(5) . . . . ? N1A S2A C2A F22A -60.8(5) . . . . ? O22B S2B N1B S1B 132.4(4) . . . . ? O21B S2B N1B S1B -6.6(6) . . . . ? C2B S2B N1B S1B -119.0(5) . . . . ? O11B S1B N1B S2B 23.6(6) . . . . ? O12B S1B N1B S2B 159.7(5) . . . . ? C1B S1B N1B S2B -91.4(5) . . . . ? O11B S1B C1B F11B 59.7(7) . . . . ? O12B S1B C1B F11B -65.6(7) . . . . ? N1B S1B C1B F11B -178.6(6) . . . . ? O11B S1B C1B F12B 175.8(5) . . . . ? O12B S1B C1B F12B 50.5(6) . . . . ? N1B S1B C1B F12B -62.4(6) . . . . ? O11B S1B C1B F13B -61.0(6) . . . . ? O12B S1B C1B F13B 173.7(5) . . . . ? N1B S1B C1B F13B 60.8(6) . . . . ? O22B S2B C2B F23B 179.4(7) . . . . ? O21B S2B C2B F23B -54.4(8) . . . . ? N1B S2B C2B F23B 67.8(8) . . . . ? O22B S2B C2B F22B 49.4(7) . . . . ? O21B S2B C2B F22B 175.6(6) . . . . ? N1B S2B C2B F22B -62.1(6) . . . . ? O22B S2B C2B F21B -64.2(6) . . . . ? O21B S2B C2B F21B 62.0(6) . . . . ? N1B S2B C2B F21B -175.8(6) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.253 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.086